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Exit Strategies for Real Estate Investors, Part 2

Published March 6, 2026

Case:

Karl was a man with the golden touch. Throughout his life, it seemed every investment idea that he touched turned to gold. Karl’s passion was real estate and he was very successful in his investments.

Karl continued to buy and sell real estate at the age of 85. His latest venture led him to a great investment property. It was a “fixer-upper” commercial building in a great area. While other buildings nearby sold for over $2 million, the seller needed to sell quickly and was asking just $1 million.

The condition of the building turned many buyers away. It was being sold “as is” but Karl was not deterred. He could see great potential with the building and knew it would not take much work to get it into market condition. Karl swooped in, bought the building for $1 million and hired contractors to refurbish the place.

After three months of hard work refurbishing the building, the building looked like new. In the end, Karl invested $250,000 in the building, bringing his total investment in the property to $1.25 million. One month after the completion of the work, Karl was contacted informally by a company that expressed an interest in the building – a $2 million interest. This was no surprise to Karl since he knew the building was a great buy.

There was one downside, however, to the idea of selling. Karl held the property for only four months, which meant the gain from the sale would be short-term capital gain. In other words, the applicable tax rate would be 40.8%, not 23.8%. Karl cringed at the thought of paying a large part of his gain in taxes. At the same time, Karl knew the real estate market could change directions in the next year. Although Karl wanted the 23.8% tax rate, he did not want to risk holding the property another eight months.

After Karl learned about the benefits of a FLIP CRUT (see “Exit Strategies for Real Estate Investors, Part 1), he eagerly wanted to move forward. It looked like the perfect solution. However, there were still two potential downsides to this plan.

Question:

What are the charitable income tax deduction rules for gifts of short-term capital gain property? If Karl moves forward with this plan, how would the FLIP CRUT payouts be taxed?

Solution:

First, pursuant to IRC Section 170(e), Karl would receive a charitable income tax deduction based upon the cost basis in the property rather than its fair market value. Section 170(e) does not allow a donor to claim a charitable income tax deduction for a property’s ordinary income element.

In this case, a fair market value calculation on $2 million would produce a tax deduction of approximately $1,480,000. However, due to the short-term capital gain on the property, Karl would instead use his basis of $1,250,000 for the calculation. As a result, his tax deduction would be about $925,000. Given his estimated AGI over the next several years, he would not have been able to deduct the full $1,480,000 anyway. On the upside, Karl would be able to deduct the entire $925,000 over the next six years. With an estimated AGI of $350,000 each year, Karl could deduct up to 50% of his AGI each year or $175,000. The 50% AGI limit applies in this case, not the 30% AGI limit, because Karl’s tax deduction would be based on cost basis.

Next, Karl discovered that the short-term capital gain of $750,000 from the sale of the property might be distributed to him over time. While it is true the FLIP CRUT would not owe any tax, the trust would report the $750,000 of short-term capital gain in tier two pursuant to the four-tier accounting rules. Therefore, it is possible that Karl’s future trust payouts would be characterized as short-term capital gain.

Again, Karl was not dissuaded with this information. First, as someone accustomed to lease income, Karl assumed most of his trust payouts would be ordinary income. Second, given the benefit of the 23.8% tax rate on qualified dividends, the trust would be invested heavily in dividend-paying stocks. As a result of this investment choice, 23.8% type tier-one income would flow out prior to any 40.8% type tier-two short-term capital gain. This would diminish the amount of tier-two income short-term capital gain realized over Karl’s life.

In the end, the positives clearly outweighed the negatives. Karl moved confidently forward and wrote another happy ending to another successful investment outing.