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

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

Greenville, SC · Member since 2015 · 6 posts · 4 votes

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
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Ashish AcharyaBusiness Member
CPA, CFP®, PFS · FL · Member since 2017 · 5k+ posts · 3k+ votes
4y

 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. 

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  • Ashish AcharyaBusiness Member
    CPA, CFP®, PFS · FL · Member since 2017 · 5k+ posts · 3k+ votes
    4y

     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. 

    INVESTOR FRIENDLY CPA®5240 Reviews
    TaxMD® | Tax Planning Software
  • Greenville, SC · Member since 2015 · 6 posts · 4 votes
    4y

    Thanks for the response! 

    1031 would be ideal. But this sales transaction took place a few years ago. Doesn't the 1031 exchange opportunity expire? 

  • Metro NY + New Bedford · Member since 2022 · 294 posts · 216 votes
    4y

    Loan any money to someone in the past?  That non-business bad debt will be a short-term capital loss.  Also, if you have any other worthless investments, now's the time to declare them worthless. Again, a short-term capital loss.

  • PA · Member since 2010 · 339 posts · 168 votes
    4y

    I’m confused. I think you are saying you sold the building 6 years ago and you offered to lend the buyer money to pay for it. The owner will need to pay capital gains, not you. The money you lent to them was your money, so you wouldn’t have to pay gains on the payoff. The interest you have been receiving is income, not a gain.

    I’m sure I am just not understanding the situation

  • Investor · Clairemont, CA · Member since 2011 · 3k+ posts · 2k+ votes
    4y

    I don't think your description was very clear, hence @Ashish Acharya suggestions. What I ended up deducing was you sold a commercial building XXX years ago and provided an owner carry back. As such you have an active installment sale with a pending payoff, which will generate a large potential CG/DR tax bill if that occurs. Your substitution of collateral idea is one you are considering in order to keep the installment sale in place and therefor continue to defer the tax bill. 

    So your questions are 1) would that actually work 2) are there any other ideas that would assist with deferring your tax bill beyond what you already suggested? 

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