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America is in the middle of its biggest-ever retirement wave. And for real estate investors who spent decades building wealth, one property at a time, the exit strategy may be the hardest deal they’ve ever had to make.
I had lunch recently with a couple I’ll call Brenda and Eddie, who are in their mid-60s, and both exhausted. They spent 30 years assembling a tidy portfolio of rental properties in the “Tony Houston” suburbs, consisting of: five houses, a small strip center and a 12-unit apartment building.
On paper, they were millionaires several times over. In practice, Eddie told me, he felt like an unpaid superintendent who couldn’t quit.
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“We were supposed to be in Italy this spring,” Brenda said. “Instead, we’re replacing a roof on one of the rental properties.”
Eddie and Brenda aren’t unusual — in fact, they’re a demographic tidal wave. What’s unusual is how few investors in their position understand all their options for getting out and how costly that blind spot can be.
The Peak 65 zone
Demographers call the period from 2024 through 2027 the “Peak 65 zone.” During this stretch, more than 4.1 million Americans are turning 65 each year — roughly 11,400 every single day.
That’s a sharp jump from the 10,000-per-day pace of the previous decade, driven by the heart of the Baby Boomer generation finally reaching the traditional retirement age.
Many of these soon-to-be retirees are real estate investors. They bought duplexes in the ’80s, apartment buildings in the ’90s and warehouses during the 2008 fire sale.
They built real wealth. But that wealth comes with strings attached, and the biggest string of all is the one no one likes to talk about: Many real estate investors feel trapped.
The three-sided trap
The trap has three walls, and most landlords don’t see all three until they’re already hemmed in.
Wall one: The tax bill. Sell a portfolio of long-held, fully depreciated properties, and the IRS is going to take a serious chunk. Federal long-term capital gains rates top out at 20%. Add the 3.8% net investment income tax (NIIT) that applies to higher earners. Then add depreciation recapture, taxed at 25%. Layer on state income taxes — which vary, but in many states run north of 5% — and the total take can exceed 40% of your gains.
For people like Eddie and Brenda, that’s a check to the government that could easily top a million dollars.
Wall two: The reinvestment problem. Even after paying the tax, you’re left with the question of where to put the money. A financial adviser may suggest a managed stock-and-bond portfolio. Under the traditional 4% withdrawal rule, $1 million in after-tax proceeds might generate $40,000 a year — a far cry from the $80,000 or $90,000 that same equity was producing in rental income.
And unlike a building, a stock portfolio can lose 30% of its value in a single quarter.
Wall three: The emotional aspect. After decades of being landlords, investors often feel trapped by their own success. They’re too tired to keep going but too smart to accept the alternatives they’ve been shown. So, they stay. They replace the roof on the next rental property. They skip Italy.
A door most investors don’t know exists
“So often times it happens that we live our lives in chains/ And we never even know we have the key.”
The Eagles weren’t singing about the U.S. tax code, but they might as well have been.
But for years, the 1031 exchange had a significant limitation for people like Eddie and Brenda: It required them to buy more property. And buying more property was exactly what they were trying to stop doing.
That changed in 2004, when IRS Revenue Ruling 2004-86 allowed interests in Delaware statutory trusts (DSTs) to qualify as replacement property in a 1031 exchange. This single ruling opened a door and transformed the retirement landscape for real estate investors.
A DST is a legal entity that holds title to real estate — typically large, institutional-quality properties such as Class A apartment complexes, medical office buildings, industrial distribution centers, self-storage portfolios, senior living communities and national-brand hotels.
Many DST offerings are capitalized at $100 million or more. Through fractional ownership, smaller investors can access these properties with minimums as low as $100,000.
The mechanics are straightforward. An investor sells their actively managed property, executes a 1031 exchange and moves the proceeds into one or more DST investments. All capital gains are deferred.
The investor transitions from being a hands-on landlord to a passive owner receiving monthly income from institutional-grade real estate. No midnight phone calls. No evictions. No tenants, toilets or trash.
Because DSTs are pass-through entities, fractional owners also participate in depreciation and amortization. That often means a significant portion of the monthly income is tax-sheltered, preserving the same tax advantage investors enjoyed when they managed properties themselves.
So, what happened to Brenda and Eddie?
They did their homework. They worked with a registered investment adviser who specialized in 1031 exchanges and DSTs. They sold the strip center and three of the five houses, executed the exchange and diversified the proceeds across four DST investments:
- A multifamily complex in the Southeast
- A medical building in Texas
- A self-storage portfolio in the Sun Belt
- An industrial warehouse leased to a national logistics company
They paid zero capital gains tax at closing. Their net worth carried forward intact, generating monthly income that exceeded what the sold properties were producing, without a single tenant to manage.
They kept the apartment building and two houses for now: planning to exchange those in a future phase when they’re ready.
They went to Italy. And — did I mention? — they didn’t write the government a check for $1 million.
Important caveats for prospective investors
DSTs are compelling, but they aren’t for everyone, and it would be irresponsible to pretend otherwise.
First, DSTs are available only to accredited investors. Under current SEC rules, that means a net worth exceeding $1 million (excluding your primary residence) or annual income exceeding $200,000 individually (or $300,000 for married couples) for each of the previous two years, with a reasonable expectation of the same going forward.
Second, DSTs are illiquid. Hold periods typically range from five to seven years. During that time, you receive income distributions but cannot access the principal.
When the real estate sponsor decides market conditions are right, the property is sold and proceeds are returned, at which point the investor can execute another 1031 exchange or recognize the gains.
Third, DST investments carry the same fundamental risks as any real estate investment: Market downturns, vacancy, property damage and interest rate shifts. The passive nature of the investment means the investor has no control over management decisions.
Finally, DSTs are SEC-regulated securities offered through broker-dealers or registered investment advisers who have been vetted by the sponsoring firms. Working with a fiduciary adviser — someone legally obligated to act in your best interest, without commissions creating conflicts — is strongly recommended.
The door is open
The 1031 exchange has survived repeated legislative attempts to cap or eliminate it. Recent legislation preserved it intact, with no limits on deferral amounts.
Combined with the DST structure, it offers a pathway that would have been unthinkable a generation ago: The ability to retire from the landlord business, defer the full tax hit and continue earning passive income from real estate you never have to manage.
For any landlords among the 11,400 Americans turning 65 today — and the 11,400 who will do the same tomorrow and the day after that — it’s a conversation worth having before the next roof needs replacing.
