58-Year-Old Landlord Says Goodbye to Tenants
How Delaware Statutory Trusts (DSTs) are helping retirees find time and freedom. Here's one couple’s story of gaining their freedom by quitting the landlord biz – without paying a massive tax bill.


Meet Frank and Linda, (not their real names). Frank and Linda have been married for 30 years and had begun having conversations around making plans for Frank to leave Corporate America before Frank turned 60. Linda would wind up her teaching career around the same time Frank would retire, and for the first time in their lives they realized that they would soon have the time they always wanted together.
Frank wanted to spend a month in Europe like he had always talked about, and Linda just wanted to go to the beach; sleep late, read books, boil shrimp and enjoy the different wines from her wine club recommendations. “Let’s do Europe in the spring when the weather is cooler,” Frank suggested, “and then we can do the entire summer at the beach when we’re ready for our warm, sunny, lazy days on the beach.” Frank’s idea sounded perfect to both.
And then it hit them: They’re not going anywhere.

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Instantly Frank and Linda re-centered around the reality of their real estate portfolio. During their careers, Frank and Linda has acquired three rental homes — a storage facility, a four-plex apartment and two vacant lots in the subdivision where they lived. Frank had watched his father speculate and gamble in the stock market and lose big more than once. Frank was currently helping his dad with medical costs and carried a bit of resentment for his dad’s fast-and-loose ways with money when his dad was younger. At 25, Frank had decided he would build his own personal wealth in real estate, something he reasoned would always be there for him; and it had. Frank and Linda's real estate portfolio, excluding their primary residence, was now valued at over $2.6 million and represented the lion's share of the wealth they would rely on for their retirement income to supplement Frank's Social Security and Linda’s pension as a teacher.
“How about we just sell it all,” Linda suggested, “After all, the market is so good right now.” This seemed like possibly a good idea to Frank. “Then we will have the time and the money to do what we want,” Linda reasoned. Frank said that sounded good but wanted to make sure he knew what the taxes would be, because he knew there could be a fair amount to pay were they to sell.
CPA Delivers Good News and Really Bad News
Frank and Linda had a long-standing relationship with a local CPA who had helped with all the accounting, bookkeeping and filings their real estate holdings had required. Frank offered to reach out to the CPA the next morning and run some numbers on what the tax bill might look like were they to sell all their investment real estate holdings.
Two weeks later Frank went to see his longtime CPA and friend, Lanny. Lanny pulled up Frank and Linda’s tax return from the previous year and started running calculations on all the real estate that the couple have been depreciating. After what seemed a solid half hour of the CPA banging on his keyboard, he looked up, squinted and leaned across his desk. “Well, I have good news, and I have not-so-good news. The good news is, you and Linda have made a lot of money on this real estate. The bad news is you’re going to get killed on capital gains taxes and depreciation recapture.”
Lanny went on to explain that since the total gains were large sums, those gains would be taxed at the current 20% capital gains rate, plus the 3.8% Net Investment Income Tax. He went on to say that depreciation recapture was taxed even higher, at 25%.
“So how bad is it?” Frank asked.
“Just over $500K,” Lanny murmured.
“You mean that Linda and I have to write a check to the IRS for more than $500K if we sell our real estate?” Frank was almost shaking.
In his head he was thinking the number might be closer to $200K, which he thought he might be able to tolerate. The very idea of writing a check to the IRS for more than half a million dollars left Frank angry, astonished and perplexed all at the same time.
How about a 1031 Exchange?
“There’s always a 1031 Exchange,” Lanny offered as what seemed to Frank a flimsy condolence. Frank knew of the 1031 Exchange, but that would just mean selling his real estate and buying other real estate that he and Linda would have to keep up with. Sure, they could sidestep $500K of tax, but he and Linda would have all the same headaches of property ownership, just with different addresses. Tenants are tenants, Frank said to himself, and all that goes with them. No, a 1031 Exchange was not going to solve their problem. Selling and buying again might look good on a spreadsheet, but it was not going to give him and Linda the freedom they wanted.
Several weeks went by for Frank and Linda without mention of their real estate assets. Then, one evening after dinner, Frank and Linda were sitting in their living room where Frank was watching baseball and Linda had her laptop out looking at travel blogs she followed online. Frank’s team was losing badly enough where he was considering turning it off. At that precise moment Linda said, “Frank, what’s a DST?”
“I don’t know, some kind of pesticide,” Frank quipped.
“Frank, it says here in this article that I’m reading that a DST is a passive form of real estate ownership that qualifies for a 1031 Exchange. The article says that many people today are opting to sell their real estate using a 1031 Exchange to move their equity into Class A apartment buildings, self-storage portfolios, medical buildings, industrial warehouses and even things like Amazon distribution centers, Walmart stores and Walgreens buildings. Apparently, these investments offer solid monthly income to investors and attractive opportunities for long-term growth,” Linda continued. “Frank, this could be it. This could be what we are looking for.”
Frank and Linda’s dilemma is not uncommon. Perhaps it was an aging population that was considered when in 2002 the state of Delaware passed the Delaware Statutory Trust Act. Revenue Ruling 2004-86 soon followed and allowed for DSTs to qualify as “Replacement Property” for the tried-and-true 1031 Exchange (part of our tax code since the 1920s). Many DSTs offered to real estate investors are capitalized with $100 million or more, and smaller investors can now access these offerings in smaller fractionalized amounts as low as $100,000. Properties include medical buildings, Class A multi-family apartment buildings, hotels, senior living, student housing, storage portfolios and industrial warehouse buildings. Nationally known tenants are typically companies like Walgreens, Hilton and Amazon, among others. Often, investors might feel better with a large and stable company like Amazon guaranteeing their monthly income, rather than the tenants who last skipped out on rent, leaving them high and dry.
Some Caveats to Consider
All real estate investing, including DSTs comes with risk, and investors should do their homework, perform their own due diligence, and read the Private Placement Memorandum, (PPM) before investing any capital. DST offerings are typically illiquid and would not be considered suitable for a large portion of someone’s wealth when liquidity is needed. Because DSTs are regulated and are “securities,” they must be purchased from a Registered Investment Adviser and/or a Broker Dealer Representative who holds a proper securities license, Series 7 or Series 65.
Many times, we are asked who can invest in a DST. Accredited Individuals and certain entities qualify. An individual must have a net worth in excess of $1 million, excluding his or her home, OR an income over $200K per year for the last two years. If married, the combined income required is $300K. The income is required to be “reasonably expected” going forward.
For the right person in the right situation, a DST might be the perfect answer to a common dilemma faced today by many real estate investors across America.
For more information, please visit www.Providentwealthllc.com or www.Provident1031.com.

Daniel Goodwin is a Kiplinger's contributor on various financial planning topics and has also been featured in U.S. News and World Report, FOX 26 News, Business Management Daily and BankRate Inc. He is the author of the book Live Smart - Retire Rich and is the Masterclass Instructor of a 1031 DST Masterclass at www.Provident1031.com. Daniel regularly gives back to his community by serving as a mentor at the Sam Houston State University College of Business. He is the Chief Investment Strategist at Provident Wealth Advisors, a Registered Investment Advisory firm in The Woodlands, Texas. Daniel's professional licenses include Series 65, 6, 63 and 22. Daniel’s gift is making the complex simple and encouraging families to take actionable steps today to pursue their financial goals of tomorrow.
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