In 1031 exchanges, the IRS doesn't categorize REIT shares as "like-kind" assets, thus precluding a direct exchange. However, investors can pivot towards a Delaware Statutory Trust (DST), which the IRS recognizes as a "like-kind" property. Under IRC Revenue Ruling 2004-86, acquiring a DST interest is the initial step. Some DSTs subsequently integrate into a REIT as part of their operational strategy. Through this evolution, investors can opt for a section 721 exchange, transitioning their DST interests into shares of the REIT's operating partnership (OP Units) on a tax-deferred basis. Typically, these OP Units hold the potential for one-for-one conversion into the REIT's common stock. It's important to note that not all DSTs follow this trajectory, and even if they do, the certainty of a UPREIT/721 exchange remains uncertain.

While the 1031 exchange into a DST and subsequent conversion to a REIT via a 721 exchange offer tax deferral benefits, significant implications demand careful consideration. Once an investor undertakes the section 721 conversion into the REIT, they forfeit future participation in 1031 exchanges with that equity. Upon divesting their REIT shares, immediate tax liabilities ensue, encompassing Federal and State Capital Gains, Depreciation Recapture Tax, and Medicare Surtax. The magnitude of these tax obligations could be substantial, particularly for investors with a history of extensive 1031 exchange utilization. Additionally, the liquidity aspect warrants attention, especially with Non-Traded or private REITs, whose illiquidity poses potential challenges. Investors must also acknowledge the inherent risks associated with Non-Traded REITs, which may outweigh the perceived benefits of tax deferral.