1031 Exchange and DST Investing Basics

1031 Exchange and DST Investing Basics

From Real Estate Development: Land to Legacy by Eugene Gershman

February 19, 2026 · 37 min · Episode 58

About this episode

Ashley Romiti discusses the basics of 1031 exchanges and DST investing with Eugene Gershman, focusing on timelines, pitfalls, and strategies for real estate investors.

Ashley Romiti breaks down how a 1031 exchange can help real estate investors defer capital gains and depreciation recapture, and why many sellers choose to roll into DSTs to simplify ownership and pursue more passive income. She and Eugene Gershman walk through the real-world 45-day identification and 180-day closing timelines, common pitfalls that can derail an exchange, and what proper due diligence looks like when evaluating DST sponsors and deals. The conversation also covers where 1031s and DSTs can fit for developers, how DST rules impact strategy, and how investors think about long-term exit planning.

People in this episode

Host: Eugene Gershman

Guest: Ashley Romiti

Topics covered

  • 1031 exchange
  • DST investing
  • real estate
  • capital gains
  • passive income
  • due diligence

Keywords

  • 1031 exchange
  • DST
  • capital gains
  • depreciation recapture
  • real estate investing
  • passive income
  • due diligence
  • exit planning

Mentioned in this episode

Organizations: DST, 1031 exchange

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