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Deal Structures

1031 Exchanges

Institutional 1031 exchange underwriting: like-kind mechanics, boot and basis math, reverse exchanges, DSTs, and the 721 UPREIT exit.

A 1031 exchange defers capital gains tax by rolling proceeds from a relinquished property into like-kind replacement property. The institutional execution is anything but mechanical. The 45-day identification window is unforgiving, and the exchange must close by day 180 or the due date (with extensions) of the taxpayer's return for that year, whichever comes first. The three identification rules constrain how aggressive a sponsor can be on substitution, and boot received in cash or debt relief triggers recognized gain in the year of exchange, up to the amount of the boot. Basis carries over into the replacement asset, which reduces depreciable basis and annual depreciation deductions and preserves the deferred gain, which the owner recognizes at a later taxable sale. When timing breaks, sponsors turn to reverse exchanges and EAT parking arrangements. When a 1031 investor cannot identify suitable property, DSTs offer passive replacement at the cost of sponsor fees and operational restrictions. The 721 UPREIT contribution is where the 1031 chain usually ends: property (often a DST interest) goes into a REIT operating partnership for OP units, swapping direct ownership for REIT exposure (listed or non-traded). OP units are partnership interests, not like-kind real property, so no further 1031 exchange follows.

These five articles walk the 1031 stack from the basic exchange through the institutional alternatives. Start with 1031 Exchange Mechanics if you are orienting on the timing rules. Boot, Basis Carryover, and Deferred Gain is the modeling workhorse. Reverse 1031 covers the parking structure when replacement closes first. DST covers passive replacement property inside the exchange, and 721 UPREIT covers the exit that ends the chain, often the step after a DST.

5 articles

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