Episode
How Tired Landlords Are Escaping $1M Tax Bills Using DST 1031 (Without Buying Another Property)
- Podcast
- The Tax Strategy Playbook
- Published
- Jun 2, 2026
- Duration seconds
- 2484
- Processing state
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Summary
Are you a tired landlord sitting on hundreds of thousands — or even millions — in capital gains and depreciation recapture, terrified of the tax bill that comes with selling? You're not alone. And there IS a better way. In this episode of The Tax Strategy Playbook, host David Wiener (Mr. Cash Flow) sits down with Tommy Olson, Vice President at Kay Properties & Investments — one of the nation's leading Delaware Statutory Trust (DST) advisory firms — to walk through exactly how investors are using DST 1031 exchanges and 721 UPREIT strategies to exit active real estate without writing a seven-figure check to the IRS. 🔑 What You'll Learn: ✅ What a Delaware Statutory Trust (DST) actually is — in plain English ✅ How to defer $800K+ in capital gains AND $300K in depreciation recapture using a 1031 exchange into a DST ✅ Why California landlords can lose up to 50% of their sale proceeds in taxes if they sell outright ✅ The real risks of DSTs that most advisors won't tell you about ✅ How a $3M commercial property sale was diversified across 6 DSTs for stable, passive income ✅ What a 721 UPREIT is and how it can provide a path to liquidity and estate planning advantages ✅ The "swap till you drop" strategy for lifetime tax deferral ✅ Who is (and isn't) a good candidate for the DST-to-UPREIT pathway ✅ The top questions to ask BEFORE you invest — and why your CPA needs to be in this conversation early 💡 Whether you're approaching retirement, burned out on property management, or just want your equity working harder without the headaches, this episode breaks down one of the most powerful — and underutilized — tax strategies available to real estate investors in 2026. 👉 Ready to explore your options? Visit kpi1031.com to access free DST resources, recorded webinars, and schedule a…