Thursday June 4, 2026

Case of the Week

Exit Strategies for Real Estate Investors, Part 5

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.

After Karl learned about the benefits of a FLIP CRUT, he eagerly wanted to move forward. (See Parts 1 and 2 for a full discussion of this decision.) It looked like the perfect solution.

Question:

However, there was still one issue unresolved. There was a $100,000 debt on the property that Karl incurred at the time of purchase. The debt is an obstacle to the successful completion of the FLIP CRUT plan. What solutions are available to remove the debt?

Solution:

Karl has at least five solutions to the debt and FLIP CRUT problem.

1. Payoff - If possible, Karl may have the resources to pay the debt and then transfer the real estate to the FLIP CRUT.

2. Release - If there is a parcel of land that may be divided under zoning rules or multiple deeds to the parcel, it may be possible to obtain a release of the debt on the entire property, leaving the debt on another portion. The released property may then be transferred to the FLIP CRUT.

3. Bridge Loan - Karl may borrow funds against other property, pay the debt on the existing property and transfer an undivided interest into the trust. When the property is sold, the undivided portion retained by Karl is used to pay the bridge loan.

4. Charity Purchase - The charitable organization may be willing to purchase part of the real property from Karl. Following this purchase, Karl has funds to pay off the debt and transfer the balance of the real property into the trust.

5. Personal Guarantee - While the IRS has not approved of this method, some have transferred an undivided percentage of encumbered property into a CRT. When the property is sold, the balance of the asset is used to pay off the debt. The donor gives a personal guarantee that the trust will not be required to pay debt. So long as the transaction works as contemplated and the property can be sold within a reasonable amount of time, this strategy may be an option. However, this strategy is more aggressive than other options and is not without risk.

Donors should consider these five potential steps in the order listed above. The technical and practical challenges increase with the latter methods. Given his choices, Karl quickly elects option one – pay off the debt. With the removal of the $100,000 debt, the unrelated business income tax and grantor trust status issues disappear. Furthermore, the future sale of the real estate will return the $100,000 “pay off amount” back to Karl. Karl is happy once again knowing that his FLIP CRUT plan is back on track.

Published March 27, 2026

Exit Strategies for Real Estate Investors, Part 4

Exit Strategies for Real Estate Investors, Part 3

Exit Strategies for Real Estate Investors, Part 2

Exit Strategies for Real Estate Investors, Part 1

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