
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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