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Defer Capital Gains Taxes Without a 1031 Starker Exchange

By TaxWealth -

A Case Study in Capital Gains Tax Deferral

Selling an appreciated asset usually triggers a large capital gains tax obligation. The timing of that tax payment, however, depends on what happens with the sale proceeds:

  • Those willing to reinvest and buy more property can defer the capital gains tax with a 1031 exchange.
  • Those not willing to keep investing in property (ready to “cash out” in other words), can also defer capital gains taxes for decades, but they need to carefully structure the sale before pulling the trigger to get that deferral.

The first option, the 1031 exchange, is well known and needs no explanation. The second option is not as well known, but is also a very effective method to defer taxes.  It is best explained using an example, so let’s step through a recent transaction that uses this tax planning approach.

Selling Property to Retire

A couple had decided to sell a four-unit rental property that they had owned for over 25 years. They were ready to retire from property ownership and wanted to sell the property outright. They announced they were “done with 1031 exchanges and property management.” The sale, though, looked like it might trigger a hefty tax bill; so, naturally, they wanted to explore every legal option to mitigate this tax damage.

They first met with their financial advisor and the tax planner (a colleague of mine.) They gave the planner the information he needed to prepare a tax analysis detailing the full tax exposure if the property was sold.

  • The property was originally purchased for $300,000, and looked to garner a sales price of about $1.25 million.
  • The property also had accumulated depreciation of $162,000 at the time of sale.
  • There was a $398,000 mortgage balance.

The couple thought the tax damage would be about $190k, which was 20% of the net on the sale ($1.250k -$300k). They soon discovered, however, that their tax problem was significantly more than that. They were unaware of other types of taxes that would be sparked by the sale, including the “Net Investment Income Surtax” and taxes due for depreciation recapture and debt-over-basis.

The Details of the Tax Obligations

Here is the Tax Analysis for the Four-Unit Property:

Projected Federal Taxes
Sales Price $1,250,000
Less: Selling Expenses -75,000
Net Sale Proceeds 1,175,000
Less: Cost Basis -300,000
Taxable Capital Gain 875,000
    Federal Capital Gains Tax @ 20% 175,000
    Net Investment Income Surtax @ 3.8% 23,750
Accumulated Depreciation 162,252
    Federal Tax @ 25% $40,563
 Debt Over Basis
Taxable Mortgage-over-Basis $260,252
    Federal Income Tax Rate @ 25% 65,063
Total Projected Federal Taxes

$ 304,766

Projected California Taxes  
Net Sale Proceeds 1,175,000
Less: Adjusted Cost Basis for California -137,748
Taxable Income 1,037,252
Plus: Debt-Over-Basis +260,252
Total Taxable Income 1,297,504
    State Tax Rate @ 12.3% $ 159,593
$ 464,359


Without a proper tax planning approach, the total taxes due for the sale of this property would have been over $464,000, nearly two and one-half times the amount the couple had expected to pay.

A Different Planning Approach

At this point, the tax planner introduced an alternative: Structuring the sale of the property using a methodology which capital asset sellers can lawfully use to walk away from escrow closing with NO immediate capital gains taxes due and receive tax-free lump sum of money that is nearly equivalent to the sale proceeds.  This happy result is accomplished by coupling a monetization loan with an installment sale: The Chief Counsel of the Internal Revenue Service stated in a 2012 memorandum that it is permissible for an installment seller to receive loan proceeds at the time of sale—even in conjunction with the sale—and not be taxed on the loan proceeds.

In addition, the sellers eliminated counter-party risk by fully relinquishing any interest in the property. Using this approach to sell the property, the ultimate buyer assumed full ownership with no recourse back to the sellers.

The upshot: The sellers solved their tax problem and received almost $390,000 more money in their pocket tax-free at closing than they would have with a straight asset sale.

They still owe the taxes, but have adjusted the timing of when they pay it to decades in the future. In the meantime, they have invested the proceeds they received at close of escrow to build wealth and generate income. They see the wisdom of using the asset growth they will earn on the deferred taxes to pay those taxes when they finally come due.  That is tax efficiency in action.


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