Trying to avoid paying heavy capital gains taxes all at once!

[Tyler R.]

Do you have a positive solution for the below situation? 

Someone is wanting to pay off a commercial building early that I financed, because they are selling the building. This person is willing to work with me to come to a solution so that I do not have to pay that huge capital gains tax at one time.

The only two solutions I know of are:

1. Substitution of Collateral – using a different building for collateral for the original loan; it will cost me about $1,000 in legal fees, etc.
   1. Continued interest (currently $1,000+/mo.)
   2. Paying less capital gains tax at once but extending over several more years
   3. It will cost about $1,000 to change
   4. Possibility of foreclosure
2. Receiving the payoff – with the increase in value and depreciation for tax purposes over the years, the capital gains are large, so the tax will be large
   1. Cash in hand
   2. I do not have to worry about foreclosure on that building (6 ½ years of paying on time, so not much worry)
   3. I can invest in rental property that I would rather own (easier to manage, better location)
   4. The building is very old and expensive to maintain, so I do not want it back
   5. The capital gains tax bill for 2022 will be large

[Ashish Acharya]

 I am sure you already thought about this: 

- Do an installment sale to manage your capital gain and NIIT taxes. 

- 1031 exchange

- if you acquire another property with cash, may be you can harness the losses with cost seg.