Matt Flower, a cash-basis taxpayer, owns an older strip mall that he acquired in 1990 in a suburb of New York City. His adjusted basis in the property is $300,000, but its FMV was estimated to be $1.4 million the last time it was appraised, which was two years ago. All depreciation Matt claimed has been under the straight-line method. On August 2, 2021, a court ordered Matt to pay $700,000 cash by November 1, 2021, to a former coworker in settlement of a sexual harassment suit. Matt finds a buyer for the strip mall in September who is willing to pay $1.2 million for the property. Matt feels that he might not find another buyer willing to pay this much and wants to sell now. However, Matt does not want to recognize any gain on the sale until at least 2022. He is sure he can borrow the $700,000 needed to pay the settlement through a short-term loan from a wealthy uncle. As his tax advisor, Matt calls you for advice. Describe at least two legitimate tax planning techniques that should allow Matt to sell his property in 2021 and defer all tax on the gain until 2022 or later.

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The two legitimate tax planning techniques that should allow Matt to sell his property in 2021 and d... View the full answer