Friday June 5, 2026
Case of the Week
Exit Strategies for Real Estate Investors, Part 10
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 nearby buildings 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 to get it to market condition. Therefore, Karl swooped in, bought the building for $1 million and instantly hired contractors to refurbish the place.
After three months of hard work refurbishing the building, the place 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. He knew the building was another great buy.
There was one downside to the idea of selling – the big tax bite on Karl’s gains. However, after Karl learned about the benefits of a FLIP CRUT, he eagerly wanted to move forward. It looked like the perfect solution. (See Part 1 for this discussion.) However, Karl’s attorney still had one question in mind.
Question:
Given Karl’s real estate investment activity over the years, could the Service argue that Karl is a developer or dealer of real estate? More importantly, could the Service win on this argument? What is the downside if Karl is classified as a developer or dealer?
Solution:
The key issue in the tax treatment of the sale of the building is whether Karl is an investor (making the building a capital asset) or is he a dealer (making the building an inventory asset). If Karl is deemed a developer or dealer of real estate with respect to this property, he will face ordinary income taxation upon sale of his property, not capital gains. In the event Karl, as a developer or dealer, decides to transfer his property to a CRT, the ordinary income component of the property will sit in tier one of the CRT after the sale of the property for four-tier taxation purposes. In addition, if the property is not a capital gain type property, the charitable deduction reduction rules will apply. This would result in lower tax savings. See IRC Sec. 170(e) and Part 2 of this series. Lastly, it would be important not to generate any unrelated business income (UBI) while the property is held inside the trust.
Because of these implications, it is preferable for donors to transfer long-term capital gain property to a CRT as opposed to ordinary income property. Nevertheless, the use of ordinary income property is still beneficial in the right circumstances. For instance, the use of ordinary income property still avoids tax on the sale of the property inside the trust and will produce a charitable income tax deduction based on the present value of the remainder interest.
Whether a donor is classified as a dealer or investor is based on a facts and circumstances test. In this case, Karl’s attorney determines that Karl is a diversified investor – art, real estate and stocks – with particular success in real estate investing. He purchases individual pieces of real estate about every three to five years and usually holds the property for five years or longer. The most common use of the property during the holding period is rental in nature.
Therefore, based upon his infrequent purchases, rental property usage, lack of any development of the property and lack of any significant property holdings, it is unlikely the Service will conclude that Karl is a developer or dealer in real estate. Typically, a person who buys and sells one property every three to five years will not rise to a developer or dealer status. Conversely, developers and dealers are actively engaged in buying, developing and selling – usually in large volumes and at great frequency. As a result of these findings, Karl’s attorney feels confident that Karl is not a developer or dealer for income tax purposes. If he holds the property for a year and a day, he will qualify for the long-term capital gain tax rate.
Previous Articles
Exit Strategies for Real Estate Investors, Part 9
Exit Strategies for Real Estate Investors, Part 8
Exit Strategies for Real Estate Investors, Part 7
