Real Estate Secrets: Mobile Home Parks & Parking Investments | Dan Pascone with Kevin Bupp | Ep #44

Mobile home parks and parking assets can be powerful cash-flow engines if you invest with the right operators. In this episode, Dan talks with real estate investor Kevin Bupp, principal and CIO of Sunrise Capital Investors, about how his firm has built a $350M+ portfolio focused on mobile home parks and parking garages/lots. Kevin explains why mobile home communities are one of the most durable forms of affordable housing, how the “tenants-own-the-home, landlord-owns-the-land” structure creates sticky, long-term residents, and why new mobile home parks almost never get built (creating a structural supply shortage). He also walks through how they buy and improve urban parking assets below replacement cost, use technology and dynamic pricing to boost returns, and underwrite for cash flow today plus “option value” from future redevelopment. The big message: investors should spend less time obsessing over which real estate niche is “best” and more time diligencing the jockey the sponsor/operator’s track record, balance sheet, and communication especially through tough market cycles.

• Who Kevin is:

  • Kevin Bupp is a lifelong real estate investor who bought his first property at age 20 while bartending and going to school.
  • Over two-plus decades, he’s owned or operated single-family rentals, apartments, industrial, self-storage, assisted living, and office.
  • Today he’s a principal and Chief Investment Officer of Sunrise Capital Investors, with roughly $350M in assets under management.
  • For the last 13–14 years, Sunrise has been highly focused on just two verticals: mobile home parks and parking (lots and garages).


• Why mobile home parks?

  • Kevin started in affordable housing (B-/C-class single-family and older apartments) and saw mobile home parks as a natural evolution.
  • They serve residents who:
    • Want to live in good school districts and “nice parts of town”
    • Value a clean, safe, quiet community
    • Don’t have the financial capacity to buy a traditional stick-built home in that zip code
  
  
  • For residents, mobile home parks are often a path to a version of the American dream: homeownership plus community, at a fraction of typical housing costs.
  
  


• How mobile home parks work (from the investor’s side):

  • Sunrise typically does not own the homes. They own:
    • The land and lots (“pads”)
    • Roads, water/sewer lines, and common infrastructure
    • Shared amenities (clubhouse, playgrounds, etc.)
  
  
  • Residents own the mobile home as personal property (like a vehicle), and pay lot rent to Sunrise for the land.
  
  
  • Mobile homes are called “mobile,” but in reality they’re rarely moved:
    • Once set, they’re blocked, anchored, and connected to utilities.
    • Moving them is complex and expensive.
    • Kevin notes that roughly 98% of homes placed in a community never leave it.
  
  
  • When residents move, they usually sell the home in place (like a single-family house), keep paying lot rent until it sells, and the new buyer takes over the lease.
  
  


• Why mobile home parks can be so stable:

  • Unlike apartments:
    • There’s rarely a “down unit” period with turns, renovations, and vacancy.
    • The home is owned and maintained by the resident, not the operator.
  
  
  • Many residents have long tenures (20, 30, even 50+ years) and pride of ownership similar to a single-family subdivision.
  
  
  • Communities are often multi-generational, with multiple branches of a family living in the same park.
  
  
  • Result: very “sticky” residents and more predictable cash flow.
  
  


• Supply/demand advantage: fewer mobile home parks every year.

  • Mobile home parks are one of the only real estate asset classes with a shrinking supply:
    • More parks are redeveloped or shut down each year than are built.
    • Kevin notes that in the prior year only six new mobile home parks were developed in the entire U.S.
  
  
  • Why so few new parks?
    • Zoning resistance: municipalities often lump all parks into the “bad park” stereotype and resist approvals.
    • Tax economics: mobile home parks usually generate lower property tax per acre than, say, apartments or retail.
  
  
  • This creates a strong structural imbalance: high and growing demand for affordable housing with very limited new supply, which is attractive for long-term investors.
  
  


• Sunrise’s mobile home park strategy:

  • Primarily buys existing communities rather than developing new ones, because entitlement is hard and lease-up risk is high.
  • Targets:
    • Quality markets with expensive housing:
      • Median home prices $250K+
      • Two-bedroom apartments renting for $2,000+/month
    
    
    • Properties with “mom-and-pop” or legacy owners (20–40+ years of ownership)
    
    
    • Communities that are structurally sound but tired and under-managed:
      • Deferred maintenance and underinvested infrastructure
      • Weak screening and collections
      • Operational inefficiencies in staffing and expenses
    
    
  
  
  • Value-add approach:
    • Upgrade infrastructure (roads, utilities, amenities)
    • Improve screening, collections, and community standards
    • Run the asset like a <strong“>true business rather than a hobby
  
  


• Staffing model for mobile home parks:

  • Every community has on-site staff.
  • Smaller parks (up to ~150 sites): often a single full-time community manager handling leases, collections, notices, vendors, etc.
  • Larger parks (Kevin’s biggest is ~700 sites) around 7 full-time staff:
    • Community manager
    • Assistant managers
    • Sales & leasing staff
    • Maintenance team
  
  
  • Above-site team includes:
    • President of operations
    • Regional VPs
    • Area managers who travel among communities
  
  


• Return targets & investor structure (mobile home parks):

  • Sunrise buys deals where, after stabilization (often 1–2 years), they can target:
    • 8% cash-on-cash return
    • 16–18% IRR over a 5-year hold
  
  
  • Typical syndication structure:
    • Preferred return: 8–10% (depending on investment size)
    • After full return of investor capital and catch-up of accrued pref:
      • 70/30 split of remaining profits (70% to limited partners, 30% to Sunrise)
    
    
  
  
  • Historically it’s taken 5–6 years to fully return investor capital and accrued preferred returns before the GP participates in carried interest.
  
  


• Geography: why they focus east of the Mississippi.

  • Most mobile home communities are on the eastern half of the U.S., across:
    • Southeast
    • Northeast
    • Portions of the Midwest
  
  
  • Only one current asset west of the Mississippi is a parking garage in Phoenix.
  
  
  • Staying relatively concentrated geographically helps:
    • Control travel time and cost
    • Support a vertically integrated operations team
    • Maintain consistent oversight and culture
  
  


• Why parking garages & lots?

  • Like mobile home parks, parking is a fragmented industry with many mom-and-pop or legacy owners.
  • Sunrise targets:
    • Urban core, high-growth cities with dense populations and strong demand drivers.
    • Examples:
      • Downtown Phoenix (one of the fastest-growing U.S. cities)
      • Old City Philadelphia, near the Liberty Bell & Independence Hall
      • Uptown Charlotte, across from the NBA’s Spectrum Center
    
    
  
  
  • Investments must:
    • Cash flow on day one
    • Offer multiple value-add levers (pricing, operations, technology, safety upgrades)
    • Be acquired below replacement cost, making them effectively irreplaceable at current build prices
  
  


• Value-add levers in parking:

  • Pricing:
    • Many garages run one static rate (e.g., “$2 per hour” all day).
    • Sunrise installs tech to enable dynamic pricing:
      • Higher rates during peak demand
      • Lower rates off-peak to keep utilization up
      • Often delivers double-digit yield improvements
    
    
  
  
  • Safety & experience:
    • Upgrading lighting (e.g., switching old halogens to bright LED) in Philadelphia made the garage feel safer at night and boosted usage.
    • Restriping, cleaning, and cosmetic improvements can quickly lift performance.
  
  
  • Air rights & future upside:
    • They look for properties where today’s use as parking is the lowest and worst use it will ever be.
    • Over time (10, 20, 30 years), the same parcel might support higher and better uses (mixed-use, multifamily, office, etc.).
    • Sunrise underwrites based on current parking cash flow but sees future redevelopment potential as “free upside”.
  
  


• How investors should choose real estate deals:

  • Kevin invests with other sponsors himself and emphasizes:
    • It’s less about the asset class (mobile home parks vs apartments vs office)
    • And more about the operator running the show
  
  
  • Every asset class can work in the right hands even office, which has been beaten up but now presents opportunistic bargains in some markets.
  
  
  • His advice: focus on the jockey, not the horse.
  
  


• What to look for in an operator (“the jockey”):

  • Track record across cycles: How did they navigate:
    • The 2008 crisis?
    • The rapid interest-rate rise period of 2022–2023?
  
  
  • Reputation & references: Talk to current investors about:
    • Actual vs. projected returns
    • Transparency
    • Responsiveness
  
  
  • Communication during bad times: Anyone can communicate when things are going well. How do they show up when:
    • Deals underperform
    • Cap rates expand
    • Unexpected repairs or vacancies hit
  
  
  • Balance sheet strength: Are they capitalized to survive downturns and avoid fire sales?
  
  
  • Ignore the “perfect” pro forma Kevin notes it will never be exactly right. Focus on the people behind it.
  
  


• Kevin’s routines, mindset, and personal notes:

  • Favorite meal for life: Steak.
  • Favorite non-phone/PC tool: Slack critical for coordinating a 50+ person team spread across the U.S., Mexico, and the Philippines.
  • Favorite success/money quote: Warren Buffett’s rule:
    • Rule #1: Don’t lose money.
    • Rule #2: Don’t forget Rule #1.
  
  
  • Favorite book: Think and Grow Rich, which he rereads regularly and gifts often.
  
  
  • Personal routine/hack: Early-morning workouts and quiet time:
    • Up around 4:30am
    • Gym 4x/week plus 2–3 road cycling sessions
    • Feels 2–3x more productive on days he trains before his family wakes up.
  
  
  • Bucket list item achieved: Owning both:
    • A home on the Gulf of Mexico
    • And a place on a nearby freshwater lake for wakeboarding, skiing, and family time fulfilling a dream sparked by childhood boating.
  
  
  • Advice to his younger self: Always surround yourself with people smarter and more talented than you on the field, in business, and in life. That’s how you grow.
  
  


• How to connect with Kevin:

  • Website: investrise.com (case studies, whitepapers, and current offerings).
  • Active on LinkedIn (primary platform), as well as Facebook and Instagram.
  • His last name is unique enough search “Kevin Bupp” and you’ll likely find the right real estate investor.

• 00:00 – Episode intro. Dan introduces himself, Tailored Wealth, and the show’s mission: real conversations to help high earners make sharper decisions so their money works as hard as they do.
• 00:22 – Topic preview. Dan tees up the discussion: the cash flow power of mobile home parks and parking garages, and how to vet operators before investing.
• 00:22–00:55 – Sponsor & show open. Tailored Wealth is introduced as sponsor, and the Making Sense of Your Money positioning is reiterated.
• 00:55 – Meet Kevin. Dan welcomes Kevin Bupp to the podcast and expresses interest in his long-running real estate background.
• 01:16–02:25 – Kevin’s backstory. Kevin explains how he got into real estate at 19–20, moved from tending bar to full-time investing, and over 20+ years has owned many asset types before focusing on mobile home parks and parking.
• 02:25–02:56 – Sunrise Capital Investors today. Kevin shares his current role as CIO and principal, and notes that Sunrise manages about $350M in assets in those two verticals.
• 02:56–04:11 – Why mobile home parks? Kevin explains how he moved from C-class single-family and apartments into mobile home parks as a natural extension of his affordable housing focus.
• 04:11–04:59 – Serving affordable housing demand. He describes the demographic they serve families wanting good schools and safe communities without the cost of traditional homeownership and why it’s personally rewarding.
• 05:24–06:23 – How parks differ from apartments. Kevin explains that Sunrise usually owns the land and infrastructure, while residents own the homes and pay lot rent, which changes the economics vs. multifamily.
• 06:23–07:20 – “Mobile” homes that don’t move. He notes that 98% of homes never leave their park, and describes the process and cost of setting them, why they usually sell in place, and how that stabilizes occupancy.
• 07:20–08:16 – Pride of ownership & community stickiness. Kevin shares examples of residents staying for decades, multiple generations living in one park, and how that compares to transient apartment rentals.
• 08:16–10:00 – Shrinking supply of parks. He explains why new mobile home parks almost never get built (zoning stigma and tax revenue considerations) and how that creates a widening supply/demand gap.
• 10:00–11:10 – Acquisition strategy: existing “mom-and-pop” parks. Sunrise prefers existing communities, often with long-time owners and deferred maintenance, where they can improve operations and infrastructure.
• 11:10–11:57 – Adding value operationally. Kevin walks through how they upgrade roads, utilities, amenities, and community standards, while also professionalizing collections, screening, and staffing.
• 11:57–13:17 – On-site staffing model. Kevin describes staff counts from small parks (~1 manager) to large (~7 FTEs) and how they support them with a vertically integrated property management team.
• 13:41–14:22 – What makes a “good deal.” Kevin outlines their target metrics: around 8% cash-on-cash at stabilization and 16–18% IRR over 5 years, layered on top of a strong location and demand story.
• 14:22–15:19 – Location and affordable housing shortage. He emphasizes markets with expensive housing and high rents, where cleaned-up parks can attract strong demand from families who have few options.
• 15:19–16:04 – Syndication structure. Kevin explains their preferred return (8–10%), 70/30 LP-GP split, and the priority of returning capital plus accrued pref before the GP participates.
• 16:31–17:23 – Geographic focus. Kevin shares why Sunrise concentrates on the eastern U.S. for mobile home parks and the one western parking deal they own in Phoenix.
• 17:23–18:56 – Why parking investments? Kevin introduces parking as a fragmented, cash-flow-driven niche, with examples in Phoenix, Philadelphia, and Charlotte, and explains their focus on urban cores.
• 18:56–19:44 – Pricing & tech upgrades. He describes moving from fixed hourly rates to dynamic pricing, adding tech, and how this can drive double-digit yield improvements.
• 19:44–20:04 – Below replacement cost & irreplaceable locations. Kevin explains why they only buy garages below replacement cost and how that gives them confidence in long-term value.
• 20:04–20:52 – Air rights & “lowest and worst use.” He discusses targeting properties where present-day parking is the lowest and worst use the site will ever have, creating long-term redevelopment optionality.
• 20:52–22:24 – Asset class vs. operator (“horse vs. jockey”). Dan asks how investors should choose real estate verticals; Kevin responds that the operator matters more than the asset class and gives examples, including opportunities in beaten-down office.
• 22:24–23:29 – Diligencing the jockey. Kevin covers evaluating track record, reputation, communication (especially in bad times), and balance sheet strength and why pro formas are never exactly right.
• 23:29–24:25 – Active vs. passive investors. He contrasts passive LPs (who choose jockeys) with active operators (who must focus on the niche they truly understand and enjoy).
• 24:25–25:49 – Transition to lightning round. Dan recaps the value of focusing on the operator and shifts to rapid-fire questions.
• 25:49–26:14 – Favorite meal & key tool. Kevin names steak as his forever meal and Slack as the non-phone/PC tool he can’t live without.
• 26:30–27:41 – Favorite quote & book. Kevin shares Buffett’s “don’t lose money” rule and talks about Think and Grow Rich as his most reread and gifted book.
• 27:41–29:15 – Morning routine & fitness. He outlines his 4:30am starts, gym workouts, road cycling, and how exercise dramatically boosts his productivity.
• 29:15–30:25 – Bucket list: life on the water. Kevin recounts his childhood love of boats and how he ultimately achieved his dream of owning both an oceanfront and a lakefront home in Florida.
• 30:25–31:44 – Advice to younger self. He shares a story about his son’s football team and uses it to illustrate the importance of surrounding yourself with people who are better than you in order to grow.
• 31:44–32:31 – How to connect & close. Kevin gives his website and social info; Dan thanks him, wraps the episode, and reminds listeners to visit makingsenseofyourmoney.com and to prioritize their own version of a rich life.

In this episode of Making Sense of Your Money, Dan sits down with veteran real estate investor Kevin Bupp to unpack two often-overlooked but powerful niches: mobile home parks and parking lots/garages. Kevin, principal and CIO of Sunrise Capital Investors, has spent over two decades investing in multiple property types and now focuses almost exclusively on these two cash-flow-focused verticals.

Kevin shares his origin story: tending bar, going to school, and buying his first rental property at age 20. Over time he expanded into apartments, industrial, self-storage, assisted living, and office, but found himself most drawn to affordable housing serving working families who need safe, clean places to live in good school districts.

That background made mobile home parks a natural evolution. They serve the same demographic as Class B-/C apartments but with a different ownership structure. In most of Sunrise’s communities, residents own their homes which are legally personal property and pay lot rent to Sunrise for the land, roads, utilities, and shared amenities. Kevin explains that despite the name, mobile homes are rarely moved; once set, they’re anchored and connected to utilities, and roughly 98% stay in the same community for life.

That “homeowner-renter hybrid” structure creates extremely sticky residents and leads to long tenures sometimes spanning 20, 30, or even 50 years, often with multiple generations living in the same community. Unlike an apartment building, Sunrise doesn’t have to renovate and “turn” units every time someone moves out, which provides remarkably stable cash flow.

Kevin then zooms out to discuss one of mobile home parks’ biggest macro tailwinds: shrinking supply. Municipalities often resist new park development due to outdated stereotypes and weaker property-tax economics per acre. As a result, more parks are being shut down or redeveloped than built each year; Kevin notes that in the prior year only six new parks were developed across the entire U.S. This creates a powerful supply/demand imbalance in a country that already faces a national affordable housing crisis.

Sunrise’s strategy is to acquire existing parks, usually with long-time “mom-and-pop” owners, in markets where housing is expensive and the shortage of affordable options is acute. They look for communities where they can upgrade infrastructure and amenities, improve operations, and still deliver compelling returns aiming for around 8% cash-on-cash at stabilization and a 16–18% IRR over a typical five-year hold. They syndicate these deals with an 8–10% preferred return to investors, a 70/30 LP-GP split after full return of capital and accrued pref, and a strong emphasis on long-term relationships.

Geographically, Sunrise focuses their mobile home park efforts on the eastern half of the U.S. (Southeast, Northeast, and parts of the Midwest) where they can efficiently support a vertically integrated operations team.

The conversation then shifts to Sunrise’s second major vertical: parking. Kevin explains that, like mobile home parks, parking is a fragmented industry with many under-optimized, legacy-owned assets. Sunrise targets urban-core garages and lots in high-growth, high-density markets such as Phoenix, Philadelphia, and Charlotte.

To create value, they look for multiple levers they can pull: pricing power (moving from static hourly rates to dynamic pricing tied to supply and demand), technology upgrades to better manage occupancy and revenue, and physical improvements that enhance safety and user experience (such as brighter, more efficient lighting and better striping). Kevin gives an example of a Philadelphia garage where decades-old lighting made customers feel unsafe at night and revenues had trended down for years. Simply upgrading the lighting and refreshing the space helped bring customers back and improved the numbers.

He also highlights a key underwriting principle: they only buy garages below replacement cost, and they seek properties with meaningful air rights and redevelopment potential. Today, parking may be the “lowest and worst use” of the land in 10, 20, or 30 years, that same parcel in a dense urban core could be far more valuable as a mixed-use development, multifamily building, or other higher-and-better use. Sunrise underwrites current cash flow based on parking, while treating that long-term upside as additional optionality.

Dan then turns the conversation toward investors: if you’re considering real estate as a passive or active investor, how should you decide where to allocate capital? Kevin’s core advice is to focus less on the specific asset class and more on the operator. In his words, it’s about the jockey, not the horse. Mobile home parks, parking, multifamily, self-storage even hard-hit office assets can all work in the right hands.

What matters is the sponsor’s track record across market cycles, their reputation and references, the strength of their balance sheet, and, crucially, how they communicate when things aren’t going according to plan. Pro formas, he notes, are never perfectly accurate; the real test is how an operator navigates volatility, interest-rate spikes, and operational challenges while protecting investor capital and being transparent along the way.

The episode wraps with a lively lightning round that reveals more of Kevin’s personal side. He’d choose steak as his one meal for life and picks Slack as the non-phone/PC technology he can’t live without for running a geographically distributed team. His favorite quote is Warren Buffett’s famous “Rule #1: Don’t lose money. Rule #2: Don’t forget Rule #1.”, and his favorite book is the classic Think and Grow Rich, which he rereads regularly and frequently gifts.

Kevin also shares his commitment to health and early-morning routines. He typically wakes around 4:30am, gets in a gym session or a road ride before his family wakes, and finds that the days he trains are 2–3 times more productive. His bucket-list achievement is deeply personal: after growing up in a modest, blue-collar home in Pennsylvania with a small family boat that sparked his love for the water, he eventually realized his dream of owning both an oceanfront home on the Gulf of Mexico and a lakefront place for watersports and family time.

His advice to his younger self and to listeners is to consistently surround yourself with people who are better than you, whether that’s on a football field or in a business setting. That’s how you grow, push your limits, and reach the next level.

Dan closes by thanking Kevin, pointing listeners to makingsenseofyourmoney.com for more episodes and resources, and reminding everyone to stay focused on their own version of a rich life.

Dan: I'm Dan Pasone, CEO of Tailored Wealth and host of the Making Sense of Your Money podcast. Real conversations to help high earners make sharper decisions so their money works as hard as they do.

Dan: This is episode number 44, and today I'm joined by Kevin Bupp to discuss the cash flow power of mobile home parks and parking garages, and how to spot the right operators before investing.

Dan: Before we dive in, make sure you're subscribed on your favorite platform. And if you find the show valuable, I'd really appreciate you leaving a quick review. Thanks so much and enjoy.

Announcer: Brought to you by Tailored Wealth, helping business leaders live their version of a rich life.

Announcer: Welcome to another edition of the Making Sense of Your Money podcast, where we cut through the financial noise and help business leaders to make smart, confident money decisions.

Dan: Kevin, thanks for joining the Making Sense of Your Money podcast. Pumped to have you today, man.

Kevin: Hey, Dan, thanks for having me here. I'm excited to be here, my friend.

Dan: Yeah, likewise. I'm intrigued by your background, and I know you've spent a long time in your space, and I think it's going to be one that really resonates with our audience specifically around the cash flow nature of what you do.

Dan: Let's start off by just giving our audience a little bit of your background and what you do and how you help people.

Kevin: Yeah, sounds good. You know, I've always been a real estate guy. I always joke and say I've never really had a “real” job.

Kevin: I got introduced to real estate back at the age of 19. I bought my first investment property at the age of 20. At the same time, I was tending bar in the evenings, going to school, and just found that real estate was something that I was excited about, that I could wrap my arms around, and that offered me the ability to make what, to me, were large checks at a fairly young age.

Kevin: So I just went all in. I kind of put all the chips on the table and started buying rental property and really haven't looked back.

Kevin: Over the years now two-plus decades I've owned just about every type of real estate. I started with single-family investments, like a lot of folks do, then evolved over time and started buying apartment buildings. I’ve dipped my toe in the water of various types of other commercial real estate: industrial, self-storage, assisted living, office you name it, I've either owned it today or have owned it historically.

Kevin: But really, for the last 13–14 years, we’ve had our eye on just two lanes. We try to stick our course and not reinvent the wheel. I started buying mobile home parks about 14 years ago and continue to buy them today under our company Sunrise Capital Investors.

Kevin: And then the other vertical that we're focused on is parking, which is fairly unique in nature parking lots, parking garages. Those are the two areas that we spend all of our time, energy, and resources in.

Kevin: I'm the Chief Investment Officer and a principal of Sunrise Capital Investors, and we've got about $350 million of assets under management in those two verticals I just mentioned.

Dan: Very, very cool. Very cool.

Dan: So I know a lot of our audience has either thought of or is actively investing in real estate in some way, shape, or form today. Why mobile home parks and parking? What got you into those two verticals, Kevin?

Kevin: Yeah, it's a great question. Mobile home parks came first, so I'll speak to that.

Kevin: I got my start and cut my teeth in when I say single-family, it was really more along the lines of Class C, B-minus / C single-family. So: affordable housing. I don't know if it necessarily had the coined identity back then as “affordable housing,” but that's what it is today and that's what we know we have a massive shortage of.

Kevin: That was the demographic that I tended to always serve, so I understand it very well. Over the years, as I started buying apartment complexes, they were basically the same type of asset: 20–30 year vintage properties that were targeting that affordable housing bucket.

Kevin: So it just seemed second nature and a natural evolution to go into mobile home parks. That's exactly who we are and who we're servicing: folks that want to be in good school districts, want to raise their families in clean, safe, quiet communities, but don’t necessarily have the financial capacity to own a stick-built home in the area code or zip codes they currently live in.

Kevin: Mobile home parks afford them the ability to live the American dream and still live in the good part of town, have their kids go to the good public schools, and so on.

Kevin: I kind of stumbled into the mobile home park space. It wasn't on purpose. I happened to meet a gentleman years back who owned a few, and I had a conversation with him. I was so intrigued by it and it seemed such a good fit for what I already knew and had been doing for 10-plus years that I figured I'd go buy one and test the theory out.

Kevin: That's what I did back in 2011. I bought that first mobile home park, wanting to either prove or disprove all the great things I had heard about the asset class.

Kevin: That first one turned into two, turned into three, and now we've owned and operated over 50 communities throughout the U.S., and it's been a fun run.

Kevin: It's very rewarding as well. We get to do well financially while helping those who really need a clean, safe, quality place to live, raise their family, and call home. It's rewarding on both fronts.

Dan: Yeah, there's a lot of similarities to what I do in that front. One of the things I love about what we do is being able to run a high-growth business but do it while you're helping people along the way, which I think is a really cool concept.

Dan: So let's unpack mobile homes and mobile parks a little bit more. I understand from the end user’s perspective why they might be attractive—you did a good job laying that out. But from an investor's perspective, what makes them different than your traditional either single-family dwellings or apartment complexes or multi-unit spaces?

Kevin: Yeah, it's a great question. They're probably the most similar to a multifamily property just think of it as a horizontal apartment complex with a few unique differences.

Kevin: One of the big ones is that typically we do not own any of the mobile homes. We own the entire community. We own the infrastructure. We own the land—roads, water lines, sewer lines, common areas, clubhouse, amenities if there are any.

Kevin: The residents actually own the mobile homes, and they essentially pay a monthly lease sometimes annually but typically monthly to lease that plot of land.

Kevin: They don't have property taxes. The home they put there is classified as chattel, so it's personal property just like your vehicle. It's tagged in the same manner. Every state handles it differently, but it's a personal piece of property. They pay a registration or annual type of tax on that. They don't pay property tax on the land.

Kevin: We pay the underlying property tax, but they pay us a monthly fee to reside there.

Kevin: The unique thing is that, while they're called mobile homes, they're not very mobile. About 98% of these mobile homes that leave a factory and end up in a community never leave that community.

Kevin: It's quite a process to get them set there. They get blocked and anchored into the ground. It's fairly costly in nature. What tends to happen is that if someone living in that mobile home decides to move, they usually just put that home up for sale like you would a stick-built home. They list it with a realtor or as a for-sale-by-owner, and they continue paying lot rent until they find a buyer. Then they move, the new buyer moves in, and assumes the financial responsibility of the ground lease payment.

Kevin: From an investor's perspective, there’s quite a bit of stability. These homes don't move out, so you don't have the normal turnover that you might have in an apartment complex. When someone moves out of an apartment, you typically have a down period where you go in and do some renovations carpet, paint, drywall repair. You might also have a month or so, once you have that unit ready, of showing it to new prospective tenants, so you’ve lost a few months of revenue.

Kevin: Whereas in our model, that's typically not the case. It's just a much more stable business model.

Kevin: On top of that, these folks are homeowners. They're very akin to residents in a single-family subdivision. This is their subdivision. They live there. We've got folks who have lived in our communities for 50-plus years. Sometimes they're multi-levels of the family hierarchy that live in one community, just like you would in a neighborhood.

Kevin: So they're very sticky residents. They stay for the long term. They've got pride of ownership. In an apartment, I'm not saying renters damage units, but they typically don't invest too much into the space it’s temporary housing before they move on.

Kevin: It's an incredibly stable business model.

Kevin: The last piece I'll mention from an investor’s perspective is that, for really two reasons, new mobile home parks don't get built. In fact, it's one of the only asset classes that has a diminishing supply.

Kevin: There are more mobile home communities that get redeveloped or shut down on an annual basis than new ones that come out of the ground new supply coming to the marketplace.

Kevin: One reason is they tend to have a bad reputation. We get lumped into a bucket that says all mobile home parks are bad, and that's just not the case. You've got the ones on the wrong side of the tracks, you've got the ones in nice hardworking neighborhoods, and you've got some really nice higher-end lifestyle communities.

Kevin: For some reason, in municipalities’ eyes, we get lumped into the bad bucket. Because of that, it's very difficult to get new zoning approval.

Kevin: The other piece is that it's just not as advantageous for a municipality from a tax perspective to approve zoning for a mobile home park. It takes up a large piece of land, and remember, these folks are not paying the typical real estate property taxes that an individual would pay on a deeded piece of land with a stick-built home.

Kevin: The municipality could do many other things with that land and probably get a higher tax basis than from a mobile home park. For those two reasons, you really don't see new ones get built. So you've got this supply-demand imbalance that is very significant in nature and advantageous for investors.

Dan: Super interesting.

Dan: I'm struck by the combination here from the tenants’ perspective they're almost a homeowner and a tenant at the same time. They own the dwelling, if you will, but they rent the land. I can see why there's a shortage in supply.

Dan: That begs the question, Kevin: how do you find these opportunities? Are you and your team typically buying existing mobile home parks, or are you developing them taking a plot of land and turning it into a community or have you done both over the years?

Kevin: The first is primarily what we do: buy existing parks. As I mentioned, it's very difficult to get approval for new builds. In fact, last year there were six mobile home parks built throughout the entire country. New development just isn't common. It doesn't happen often, and it’s very risky.

Kevin: Even if you could get a piece of land rezoned and approved to build a new mobile home park, then you’ve got lease-up risk and things of that nature. It's like a subdivision you build it out in phases and it takes time to actually start getting cash flow.

Kevin: We're really focused on buying existing properties, for the most part. We like to buy assets that are in great markets and have historically been owned by maybe a mom-and-pop owner a legacy owner who's had them for 20, 30, 40 years. That's a pretty common profile of our seller. Maybe they weren't the original developer, but maybe they're second or third in line, and they've just owned it for quite some time.

Kevin: What we tend to find is they stop pouring a lot of capital back in. They don't do a great job of setting forth capital improvement budgets on an annual basis. These properties just get tired over time.

Kevin: We can go in, breathe new life into them, redo infrastructure, put new roads in, upgrade amenities, build playgrounds, build clubhouses just create a better lifestyle for the residents who are living there. In turn, we operate them a lot more efficiently as well.

Kevin: We really run them like a true business, rather than how a lot of mom-and-pops do, where they might not have great qualification standards for new residents, might not do a great job of collections, and might have payroll inefficiencies with staffing and things of that nature.

Kevin: So we buy existing product that we know we can improve upon and add a lot of value to.

Dan: Got it. And what type of staffing does it take to effectively run these types of properties?

Kevin: Yeah, it's a great question. It can range from as little as just one person on-site. Every one of our communities has on-site staff. Up to about 150 sites in size, we would have a full-time community manager 40 hours a week, one individual who handles collections, hands out notices, dispatches repairs and maintenance calls, handles vendors, and so on.

Kevin: Above that size, we might add an assistant manager a part-time assistant manager. I'd say the largest community we have is about 700 sites, and that one has, I think, seven total full-time staff.

Kevin: It’s got a full-time community manager, two assistant managers, two sales and leasing agents, and one or two full-time maintenance staff as well. So that's about the two sides of the spectrum: one to maybe seven or eight on the largest scale.

Dan: All right. So let's talk about the financial side of these. What makes a good deal in this space? And how are you managing either investor cash flow or your own cash flow? Give us a look under the hood of a deal and some of the return expectations.

Kevin: Yeah. A “deal” can be defined differently depending on who you talk to. We have certain metrics we want to hit for our investors and for the funds that we have.

Kevin: For us, we want to know that upon stabilization which for most communities we buy will take anywhere between one and two years to get to a point where we feel it's financially stable we can achieve, from that property, somewhere in the realm of an 8% cash-on-cash return, and that over a five-year hold we're able to achieve roughly a 16–18% internal rate of return.

Kevin: That helps us define the general buy box. But it's more than just that. I'd say before we even start looking at financial metrics, we want to know we're in the right location. Location is everything in real estate, so location always comes first.

Kevin: We can hit those financial returns and metrics in a lot of areas across the country where we would choose not to buy. We want to be in areas that truly have a massive shortage of affordable housing. It's a national crisis, but it's emphasized in some markets more than others.

Kevin: There are parts of this country where it's still pretty affordable to live you can live in many areas of the Midwest fairly affordably. We want to buy in markets where median home prices are $250,000-plus, where a two-bedroom apartment rents for over $2,000 a month.

Kevin: We want to know we can go in, breathe new life into these communities, even if there’s a really bad element that has been there because the park was run poorly for two decades. We can clean house, because we know there are endless amounts of people who will be waiting to move in once we clean it up and do a good job because there's nowhere else in that local marketplace they can afford to live in a place like that.

Kevin: So that’s the general overview of how we think about cash flow and operating our funds. From a structure standpoint, we're pretty standard.

Kevin: If someone listening is familiar with real estate syndications, we basically run a model with a preferred return structure in place. That varies from 8% to 10% depending on the size of the capital investment. Then we have a 70/30 split 70% to our limited partners, our passive investors, and 30% to us.

Kevin: That’s only after we actually do a full return of capital and make up any accrued preferred return. On our general partner side, historically it's taken us roughly five to six years to do a full return of capital and catch up on any preferred returns that have accrued over that period of time. Only at that point do we participate in the carried interest of the investment.

Dan: Got it. Okay, makes sense.

Dan: Do you focus on any specific geographies? Are you looking across the whole country for that dynamic of high quality of living but lack of affordable housing?

Kevin: You know, just from a logistical standpoint, we tend to stay on the eastern side of the Mississippi.

Kevin: We've got quite a few communities in the Southeast as well as the Northeast, and we've got a few in Midwestern states. We only own one property today that is on the other side of the Mississippi, and that's actually a parking investment a parking garage in Phoenix.

Kevin: For the communities, we want to have some type of efficiency with our staffing. We've got a full property management team that's vertically integrated: a president of operations, regional vice presidents underneath him, area managers who travel around these different communities and oversee the community managers and their staff.

Kevin: If we were more spread out across the entire country something in Washington State, something in California, something in Arizona, something in Montana—it gets fairly cost-prohibitive to be traveling around. It takes a lot of time.

Kevin: For that reason, we tend to concentrate our efforts on the eastern half of the U.S.

Dan: Makes sense. Makes sense.

Dan: All right, you mentioned parking. Let's shift gears to the second aspect of your business. Tell me a little bit about what you look for there and how that compares as an investment to the mobile home parks.

Kevin: Yeah. So it's all about cash flow again kind of the same thing.

Kevin: Parking investments are a very fragmented industry, just like mobile home parks, with lots of mom-and-pops and old legacy owners who own these properties.

Kevin: For parking, it's slightly different as far as location. We want to be in urban-core, high-growth markets. I mentioned Phoenix—we own a property right in downtown Phoenix, one of the fastest growing cities in the country. We just bought a property a couple months ago in Old Town Philadelphia, a block away from the Liberty Bell and Independence Hall and those local tourist attractions.

Kevin: We bought one at the end of last year across from the Spectrum Center in uptown Charlotte.

Kevin: We really look for locations that are high-growth markets and highly densely populated areas. We also want to know there are some levers we can pull going in to add value. We want to buy a stable asset, but one with multiple value-add levers we can pull.

Kevin: A lot of those come down to pricing levers seeing a delta between where they're currently priced and where the market is. There’s also additional technology we can put in place that allows us to run a dynamic pricing model.

Kevin: Historically, the garage might have always run on a fixed pricing model $2 an hour no matter what time of day you come. Whereas we can follow demand supply/demand timeframes and charge more when demand is incredibly high and charge lower when demand is low.

Kevin: We can adjust that and really increase our yield quite a bit, sometimes double digits, just by putting some of those changes in place.

Kevin: Some of the other simple things we do: we bought this garage in Philadelphia and, after surveying parkers and the nearby office buildings and hotels that use our garage, we found they hadn’t upgraded the lighting in like 10 years. Half the lights were burnt out. They had old halogen lighting that, number one, was not energy efficient, and number two, wasn’t very bright.

Kevin: Folks did not feel safe after 6:00 or 7:00 in the evening parking there. We had seen a drop-off in the P&Ls over the last six years, and honestly we attributed a portion of that to the lighting.

Kevin: We've upgraded the lighting, cleaned it up, restriped lines, and we've seen a massive rebound just over the last four months from those minor improvements. Simple things, but powerful.

Kevin: How we look at parking is this: it has to be cash flowing day one. We need to be able to pull those value levers. But I think the most important thing that excites us about this asset class is that everything we purchase is below replacement cost.

Kevin: We would not be able to rebuild any of these parking structures today, with the cost of labor and materials, for what we've paid. So it's somewhat irreplaceable real estate.

Kevin: Second, we want to know we have air rights, and we want to know that the use today as parking is the lowest use it will ever be meaning it will only ever have a higher and better use at some point in the future. It's parking today and might be parking for 10 or 15 years, but at some point in time that parcel in this densely populated urban core will have a higher and better use.

Kevin: We don't underwrite that future, but we know it will inevitably be there. Until that point, we can cash flow and do quite well using it as parking in its current use. So it's a great asset today with a very bright future at some point, whether that’s a decade or two or three from now.

Dan: Very cool. Well said.

Dan: All right, you've been in all aspects of real estate now, so I think this is an interesting question to ask. Put yourself in the investor's shoes. You've been the chef, so to speak, helping to source these deals and understand what makes them good investments.

Dan: If you're an investor who's looking to invest in real estate maybe you're already doing so lightly, maybe you're doing syndications, maybe you've rented a few properties how would you evaluate which verticals of the real estate industry would be best to invest in based on your specific investor profile?

Kevin: Yeah, that's a great question. I can speak from the other side of the table. I've got a number of investments with other groups that run different types of property.

Kevin: I’ll say it's not a function of which asset class or what’s the best vehicle today is it parking, mobile home parks, multifamily? I think they're all great in their own way, and you can make a lot of money and generate great returns in any asset class even office.

Kevin: Office has really been frowned upon, but it's turning around in a number of markets where it's hit bottom. You're able to buy office properties at very opportunistic levels. Some opportunistic funds have rolled out big institutional groups have rolled out $500 million or $1 billion funds to buy office now, because inevitably it will rebound. It might not ever get back to pre-COVID levels, but it will recover.

Kevin: So I think it's more about the operator, the sponsor you’re investing with the jockey, not necessarily the horse.

Kevin: You really need to understand who's running the show and how long they've been doing it. What does their track record look like?

Kevin: We're in a cycle right now where interest rates went up to multi-decade highs at an incredibly fast pace. A lot of investment groups found themselves in challenging situations. 2008 was another period like that.

Kevin: You really need to look back and study the track record and the reputation of the group you're investing with. How have they managed good times? How have they managed bad times? What’s their communication like? Talk to other investors who have capital with them and find out what their experience has been.

Kevin: It's not about when things are going great. It's about when things aren't going so great, when you have not-so-great news. I don't care how great of an investment group you are you’re going to have a period where there's not-so-great news to share with your investor base.

Kevin: How do you communicate? How often do you communicate? How effectively do you communicate? Those are all important things to look for.

Kevin: How strong is the balance sheet of the investment group you're looking at?

Kevin: Forget about all the beautiful marketing material and the pro forma. The one thing I can promise you about a pro forma is it will never be correct. I don't care how stellar of a track record a group has. It's either going to exceed expectations or miss them sometimes miss them significantly.

Kevin: Really understand the person that's running the show get in alignment with them and make sure you're comfortable with their track record, history, and balance sheet. Forget about the investment itself that they're focusing on. If they've got a winning track record and a solid reputation over multiple decades, then I’d say your money is probably fairly safe much safer than with someone who's just getting into the business and might have a seemingly great deal but not the decades of experience of running through market cycles, managing capital effectively, and all those other things.

Kevin: So really, it's all about the jockey.

Dan: I like that. So the jockey is the team you’re hiring for the syndication or group, and the horse is the asset, right?

Dan: What I kind of hear you saying is: if you're passively investing in real estate let's take out the people actually doing the rentals day-to-day or managing the property if you're passively investing, it matters probably a little bit less about the horse. You can buy horses in a lot of different racing parks, if you will. It’s the jockey being able to find the group that's going to provide you the best returns and stable yields.

Kevin: That's right. Absolutely.

Kevin: If you're actively investing if you're out there buying your own real estate I think the same thing holds true. Where does your expertise lie? You can make money in anything; it's about whether you understand it and are excited about it, and whether you want full accountability for seeing the business plan through.

Kevin: Again, you can make money in any of these asset classes. I'll make the argument that I think mobile home parks and parking are the best, but I'm a little biased.

Dan: Sure. Sure. All right, cool, man. That's great.

Dan: All right, we're going to shift gears now. We're going to get to know you a little bit better. We're going to bring you into the lightning round, Kevin, which is all about you sharing the first thought that comes to your mind.

Dan: I've got some questions for you. It could be a one-word answer, it could be a long drawn-out thought, or anywhere in between. You ready to roll?

Kevin: Let's go.

Dan: Let's go.

Dan: All right, one meal for the rest of your life. What is it?

Kevin: Steak.

Dan: Steak, all right.

Dan: What's one tool or piece of technology could be hardware or software other than your computer or your phone that you can't live without?

Kevin: I'd say, from a company perspective, we leverage Slack. We're a team of about 50 folks on an international level, and we can maintain communication effectively using Slack.

Dan: Yep, I do the same thing. Your team is spread out all over the place?

Kevin: All over the U.S., Mexico, and the Philippines. We're all over the map. It's myself and the other principal of our group, Brian and me—Brian Spear and myself—who live here in Tampa. Then we've got about 70 other folks who live in the U.S. and about 15 who are international. But Slack is it.

Dan: Love it. Love it.

Dan: Do you have a favorite quote or phrase about money or success?

Kevin: Yeah, that's a good one. I love Warren Buffett. I love everything he’s about, and I always mess this up, but his rule is basically about not losing money.

Kevin: Rule number one is: don't lose money. Rule number two is: don't forget rule number one.

Dan: Refer back to rule number one. Yeah, that's it.

Dan: All right, I like it. I like it.

Dan: This is going to be an interesting one because I see you've got a book behind you. Do you have a favorite book on finance or business?

Kevin: You know, it's about the only book I read on an annual basis. I reread it maybe not the entire way through, but I definitely use it as a resource manual and I've probably done that for the last 15 years. It’s Think and Grow Rich.

Kevin: It's not necessarily finance-specific, but it's a classic. There’s always a golden nugget or lesson you can pull out of it the second, third, fourth, fifth, sixth time around. It's a great one, and it's probably the book I've gifted more than any other to friends, family, and colleagues.

Dan: It is an absolute classic. Couldn't agree more with that. I actually did a LinkedIn post about that book a couple weeks ago, so I like it.

Dan: Do you have a personal routine or a hack that you could share with our audience?

Kevin: I don't know if I have a “hack” per se, but I'm really into health and fitness. Having a structured fitness regimen really starts my day off on the right foot, and I feel like on the days I miss it whether due to travel or something that interrupts the flow and I can't get a workout in those are the days I'm the least productive.

Kevin: I feel like I get 2x the amount of work done, maybe sometimes 3x, on the days I get a good workout in first thing in the morning. I get up before the rest of the family gets up normally wake up at 4:30 in the morning, get my workout in, get some quiet time, have a coffee or tea, and sit and prepare for the day before anyone gets up and the chaos starts in the household.

Kevin: For me, that works really well. The days that it doesn't happen the days I sleep in, or get up when the kids get up and my wife gets up and it's chaos right out of the gate those are the days that are I mean, I’ll get stuff done, but it just doesn't feel the same. It doesn't feel like it flows as well.

Dan: You and I are similar on that. What do your workouts look like? What are you into from an exercise perspective?

Kevin: I do gym workouts normally four days a week, and I'm really into road cycling that's been a passion of mine for a couple decades. Two to three days a week I'll get out and crank out a couple of hours early in the morning on the bike, feel the wind through my hair, get out and smell the fresh air, and listen to a podcast or music and just zone out.

Dan: Love it. Yep, can't beat that. I'm with you on that. It's a great way to start the day. I agree.

Dan: What's one bucket list item you've already accomplished?

Kevin: Yeah, that's a great question. When I was in my early years, I grew up in Pennsylvania. We didn't grow up wealthy—very middle of the road, blue-collar, both parents worked.

Kevin: At the age of 10, my parents bought a little boat a tiny boat. We had a little river about an hour away from us. We'd go there, and they owned the boat for two or three years. That really turned on my love for the water and boating and everything that revolves around that.

Kevin: From that point forward, I was just enthralled with the idea of living by a body of water. When I moved to Florida at age 22, my dream was because I love the ocean and freshwater equally, and there’s quite a bit of both down heremy dream was to have a property on the ocean and another on a lake nearby.

Kevin: We were able to accomplish that in the last four years. We've got a little bit of both. We get to experience wakeboarding, waterskiing, and all that fun stuff on the lake about an hour away, and then we've got our home here on the Gulf of Mexico.

Dan: Awesome. Can't beat that. You get a little bit of both therevery cool.

Dan: All right, last one. If you could give advice to your younger self, what would it be?

Kevin: I'd say surround yourself with folks who are smarter than you.

Kevin: I literally had this conversation with my son this morning. It’s not a direct correlation with “smarter,” but he just got into tackle football this year. They're going to states this week they’re phenomenal, undefeated, and just killers. All the kids on the team are great.

Kevin: He's 11 years old and he's by no means the best on the team. He doesn't get a lot of playtime, but I'm like, “Man, this is an amazing experience to be a part of. I know it gets frustrating that you're not getting as many plays in. You show up at practice and you show up every day, but there are some incredibly talented kids on that team.”

Kevin: I told him, “It's a good thing. Watch what they do, how they do it, why they do it. Talk to them about what they're doing. Talk to them about the plays and what they think. Get in their head. You definitely want to be around those who are way more talented than you and extract as much as you can from that.

Kevin: It's better than being the best on a team where you don't have anywhere to grow. You can’t grow as an individual unless you're constantly uncomfortable, pushing yourself to be better, and trying to live up to some of the others on your squad.”

Kevin: I think that applies to life whether it’s friends, business just be around those who help push you and push you to grow and be a better person.

Dan: I love it. Well said, man.

Dan: Kevin, if our audience wants to connect with you, collaborate, or learn more about you and your team, where can they find you?

Kevin: You can go to our website: investrise.com. We've got information about any available opportunities. We've also got a lot of case studies on there. We have whitepapers we share on our investment thesis.

Kevin: Even if you don't have an interest in investing, there’s probably some stuff there you can grab that's free and informational.

Kevin: I'm pretty active on LinkedIn as well as Facebook and Instagram, but I'd say LinkedIn is where I'm most active. I wish I could give out my handle, but it's different on each platform. My last name is unique enough it's Bupp that if you just type in “Kevin Bupp,” I'm pretty sure I'm the only one who's going to come up as a real estate investor.

Dan: Awesome. Well, that's great, Kevin. Thanks for coming on, man. Appreciate having you and sharing your insights today.

Kevin: Thanks for having me, Dan. It's been a pleasure.

Dan: You bet.

Dan: And that's it for the episode. You can find our podcast along with our newsletter and our YouTube channel, all for free, at makingsenseofyourmoney.com. And as always, prioritize your version of a rich life.

• Sunrise Capital Investors: Kevin’s real estate investment firm focusing on mobile home parks and parking assets.
• Mobile home parks: A niche within affordable housing where residents typically own their homes and rent the underlying land.
• Parking investments: Includes parking garages and surface lots in urban cores, often with value-add potential through pricing, technology, and operations.
• Think and Grow Rich: The classic mindset and personal development book Kevin rereads regularly.
• Tailored Wealth: Dan’s advisory firm, helping high earners build coordinated, goal-aligned financial plans.

• Tailored Wealth – Work with Dan and the team
• Making Sense of Your Money – Podcast Archive
• Resources for Business Owners & Professionals
• Contact Tailored Wealth

If you’re curious about investing in real estate niches like mobile home parks or parking, consider:

• Clarify your role: Decide whether you want to be a passive investor (LP) or an active operator.

  • Passive: focus on diligencing the jockey the operator’s track record, communication, and alignment.
  • Active: focus on the niche you understand best and can commit to mastering.


• Assess your risk tolerance and time horizon: Cash-flow-focused assets like mobile home parks and parking can be attractive for long-term income, but they’re still subject to market cycles.


• Review potential operators: Ask about:

  • Performance across multiple deals and cycles
  • How they handled difficult periods (rate shocks, vacancies, etc.)
  • How frequently and transparently they communicate with investors


• Integrate with your overall plan: Work with a firm like Tailored Wealth to determine how illiquid real estate fits into your broader retirement, tax, and liquidity needs.


• Stay educated: Listen to more episodes of Making Sense of Your Money, explore additional resources, and keep refining your investing framework over time.

When you’re ready, connect with qualified professionals to explore whether and how these types of investments could fit into your version of a rich life.