Real Estate Investing for Cash Flow with Kevin Bupp

Senior living investments are at a critical inflection point. Demand is sharply rising as the Baby Boomer generation ages, but supply hasn’t kept pace. The “silver tsunami” is starting to send waves our way, and skilled operators are already taking advantage. Value-add senior living investments, like the example shared by today’s guest, are seeing values multiply—and diligent operators have huge opportunities not only to make sizable returns but also to provide better lives for their residents.

Lynn Jerath, founder of Citrine Investment Group, has a battle-tested background in REIT investing, hospitality, multifamily, and real estate private equity. She’s pivoted to senior housing investments not only because of the profit potential, but also because of the purpose behind them. And she’s not just buying managerially distressed assets, flipping the operator, and walking away.

Lynn’s team is delivering significant value add and, as a result, increasing the facility's value by 2x–3x on their total investment. She says demand is still growing while supply is constrained—and this trend could accelerate. 

Between independent living, assisted living, memory care, and active adult investments, Lynn proves (with real numbers) that this space is far from saturated as the silver surge begins to wash ashore. 

Insights from today’s episode:

Real return numbers on senior living investments as Lynn operates heavy value-add improvements 

Why senior living has a long road ahead as demand grows and supply stagnates 

Thinking of going from multifamily to senior living? Lynn has crucial advice to share 

The #1 way to get more senior living residents in your community 

Most popular niches of senior living (and their current cap rates) 

Lynn’s exact buy box for senior living investments—what has to work for her to buy  

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Connect with Lynn on LinkedIn

Citrine Investment Group

Recommended Resources:

Accredited Investors, you’re invited to Join the Cashflow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club!

If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, go to InvestWithKB.com for opportunities to invest in real estate projects alongside Kevin and his team. 

Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com. 

Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast.

00:00 Intro

01:54 Senior Living is a Different Ballgame

07:18 Undersupplied with Growing Demand?

13:59 Why Senior Living CAN'T Be Replaced

21:15 Big Players Are Getting In

24:52 Value-Add Senior Living in 2026

28:12 Case Study (2Xing Value)

31:07 How to Value-Add Senior Living

35:27 Getting New Residents

37:44 Most Popular Niches (and Cap Rates)

42:05 Lynn's Buy Box

47:55 It's About More Than Money

49:39 Connect with Lynn!

Mobile home parks are often labeled “recession-proof,” and it’s largely true. They were some of the most resilient assets throughout the Great Financial Crisis, when single-family homes, multifamily apartments, and most other asset classes saw deep distress.

But what is it about mobile home parks that make them seemingly “safe,” and is there a catch?

Jack Martin, co-founder and CIO of 52TEN, was investing in real estate before, during, and after the 2008 housing market crash, and the fallout caused him to reconsider where he wanted to invest for the next 10, 20, or 30 years.

In this episode, he shares exactly why he pivoted from multifamily apartments to “safer,” more recession-resistant mobile home parks, and delivers crucial advice on gauging market demand, “conservative” underwriting, and scaling your investments in today’s market.

The truth is, mobile home parks are strong investments, but only with good operators. Those who understand the asset, market, and tenant dynamics usually stay profitable—even in a worst-case scenario. But those who underwrite mobile home parks just like they would any other real estate asset are in for a rude awakening.

Insights from today’s episode:

Why Jack exited multifamily apartments for mobile home parks after 2008

Why mobile home parks are more “recession-proof” than other asset classes

Practical ways to gauge mobile home park demand in a new market

The three biggest challenges mobile home park investors face in 2026

Why “cheaper” is rarely better when buying a mobile home park

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Connect with Jack on LinkedIn

52TEN

Recommended Resources:

Accredited Investors, you’re invited to Join the Cashflow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club!

If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, go to InvestWithKB.com for opportunities to invest in real estate projects alongside Kevin and his team. 

Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com. 

Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast.

0:00 Intro

0:58 Jack's Investing Journey

3:52 The Fallout of 2008

10:17 Pivoting to Mobile Home Parks

18:14 "Recession-Proof" Assets

28:10 Gauging Market Demand

36:19 "Painful" Lessons Learned

48:33 Connect with Jack!

Over the last few years, many real estate investors learned a painful lesson: a polished pitch deck and impressive projections don’t guarantee a “safe” investment. Deals went south, capital got stuck, and naturally, passive investors are now far more cautious about where they deploy their hard-earned money.

Sarah Miskelly, founder of Hylee Capital, has witnessed this shift firsthand. Today, smart limited partners are no longer chasing flashy pro formas. They want risk-mitigated, institutional-grade opportunities that once felt out of reach for everyday investors. At the same time, there’s been a growing shift toward debt investments, many of which Sarah believes aren’t nearly as safe as they appear.

Sarah shares how she evaluates sponsors and syndication deals through both the “hard” and “soft” sides of due diligence, along with the red flags she watches for—mistakes that have burned countless LPs in the past. She also breaks down the return metrics that matter most to hands-off investors and highlights the most compelling opportunities emerging in today’s housing market—from multifamily apartments to mobile home parks.

Insights from today’s episode:

Sarah’s step-by-step process for vetting operators and syndication deals

The return metrics that matter most to passive investors in today’s market

Why many LPs are moving toward debt investments (that aren’t as safe as advertised)

How to build a resilient portfolio by blending high-IRR deals and steady cash flow

How building multiple cash flow streams can lead to greater lifestyle freedom

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Connect with Sarah on LinkedIn

Hylee Capital

Recommended Resources:

Accredited Investors, you’re invited to Join the Cashflow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club!

If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, go to InvestWithKB.com for opportunities to invest in real estate projects alongside Kevin and his team. 

Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com. 

Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast.

0:00 Intro

0:49 Total Lifestyle Freedom

9:02 Better "Hands-Off" Investments

10:54 Operator Red Flags

18:54 What Has Changed?

22:39 LPs Are Being "Cautious"

28:44 Playing "the Long Game"

37:00 2026's Biggest Opportunities

40:49 Connect with Sarah!

In multifamily real estate, it used to be that “a rising tide lifts all boats.” In this market cycle, that’s no longer the case. Apartment deals aren’t profitable by luck. They’re run by disciplined operators who understand the difference between surface-level updates and deep, value-add strategies that drive tenant retention, rent growth, and higher returns.

After starting his career as an architect, Mark Shuler transitioned into ownership and development, and today, he leads a private equity firm that delivers sizable returns to passive investors through value-add multifamily properties. Mark has overseen thousands of apartment units and over $600 million in assets under management, so he understands, better than most, what actually moves the needle on NOI.

When interest rates rose and cap rates followed suit, multifamily valuations tanked. Will there be more turbulence in 2026, or should operators and limited partners prepare for some of the best buying opportunities we’ve seen in years? Mark provides insights on the industry “reset” that’s taking shape, addresses the red flags that too many investors overlook when analyzing deals, and even shares about his latest real estate-adjacent venture—a pure cash flow play that complements his long-term multifamily investments.

Insights from today’s episode:

High-ROI property upgrades that actually move the needle for multifamily investors

Common deal “killers” that operators often miss during due diligence

The biggest risks and opportunities that multifamily investors face in 2026

Why strong multifamily operators are thriving amid an industry “reset”

Regulatory pressure that is forcing operators out of certain markets

Lessons from managing thousands of apartments and $600 million in assets

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Connect with Mark on LinkedIn

Email Mark at: [email protected] or [email protected]

Recommended Resources:

Accredited Investors, you’re invited to Join the Cashflow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club!

If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, go to InvestWithKB.com for opportunities to invest in real estate projects alongside Kevin and his team. 

Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com. 

Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast.

Chapters: 

0:00 Intro

0:56 What Is "Value-Add" in 2026?

6:46 Multifamily Red Flags & "Dealbreakers"

13:14 Regulatory Pressure on Operators

17:46 2026 Opportunities & Risks

24:27 Mark's Latest Business Venture

32:42 Connect with Mark!

Imagine replacing an entire rental property portfolio with just one “small” commercial asset. You can either manage 80+ rental units or just one building, with a fraction of the tenants, turnover, and headaches.

Saul Zenkevicius did just that. He netted $250,000/year in cash flow from one small bay industrial real estate deal which quickly replaced the entire cash flow from a rental property portfolio he’d built over the years. 

These small bay properties still have strong demand in most markets, with limited supply, and durable cash flow potential that institutional investors are finally starting to recognize. Saul made the leap and is now investing heavily in the small bay sector. He shares his exact buy box, the demographic signs of a strong market, and the biggest mistakes beginners can make in small bay warehouses. 

Saul's contrarian thinking doesn't stop at small bay. We get his profitable take on why malls may be the most underrated investing play around. He’s got real numbers to back it up—malls aren’t dead; instead, they can be converted into cash flow machines. 

Insights from today’s episode:

How Saul replaced an 86-unit rental portfolio with just one small bay investment 

Still undersupplied? Why small bay may see strong demand for decades to come 

Saul’s point-by-point buy box of what to look for when buying a small bay warehouse 

Mall conversions: Saul’s contrarian investment strategy that’s seeing huge payoffs 

The market conditions that destroy small bay cash flow—and Saul's exact process for avoiding them

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Connect with Saul on LinkedIn

Sign Up for Saul’s Newsletter

Recommended Resources:

Accredited Investors, you’re invited to Join the Cashflow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club!

If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, go to InvestWithKB.com for opportunities to invest in real estate projects alongside Kevin and his team. 

Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com. 

Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast.