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A Clear Introduction to 1031 Exchanges, DSTs, and Real Estate Exit Planning

This guide was created for long-time property owners who are considering a sale, planning a 1031 exchange, or exploring how to transition from active to passive real estate management.

1031 exchange dst ebook

What This Guide Covers

This is not a promotional brochure. It is an education-first resource designed to help real estate investors understand their options before decisions are forced by timelines or taxes.
Inside the guide, you’ll learn:

  • What Delaware Statutory Trusts (DSTs) are and how they work
  • How 1031 exchanges, DSTs, and 721 UPREITs can fit together in a long-term strategy
  • How retiring landlords transition from active management to passive income
  • The lifecycle of a DST investment, including income and exit considerations
  • How debt replacement, leverage, and depreciation impact after-tax outcomes
  • Common mistakes investors make when selling long-held property
  • Case examples showing how investors diversified and simplified ownership


The goal is to provide clarity, context, and better questions to ask—not to push any specific
investment.

Who This Guide Is For

This guide is designed for:

  • Retiring and transitioning landlords
  • Long-term property owners considering a sale
  • Investors facing a potential 1031 exchange
  • Families planning estate and legacy transitions

If you are early in the process, this guide helps you plan thoughtfully.
If you are further along, it helps ensure decisions are made with full understanding.

My Approach

I believe DSTs and 1031 exchanges should never be treated as one-size-fits-all solutions. Instead, they should be evaluated as tools within a broader real estate exit strategy.
Real Estate First: Every recommendation begins with the real estate itself. I evaluate DST offerings with the same lens I used when underwriting direct investments—focusing on fundamentals rather than marketing narratives.

Education Before Execution: I prioritize education so investors understand how each strategy works, the trade-offs involved, and the risks. Clients are encouraged to ask questions and take the time they need before making decisions.

Portfolio Thinking: Rather than recommending individual transactions in isolation, I help investors think in terms of portfolio construction, diversification, income sustainability, leverage, and long-term flexibility.

Conservative, Disciplined Analysis: I favor established sponsors and disciplined
underwriting assumptions, particularly for investors approaching or in retirement, who often prioritize capital preservation and income stability.

Collaboration With Existing Advisors: I work alongside clients’ CPAs, attorneys, and Qualified Intermediaries to ensure strategies are aligned, timelines are respected, and decisions are fully informed.

Who I Work With

I primarily work with:

    • Retiring and transitioning landlords
    • Long-term property owners preparing for a sale
    • Investors seeking to simplify ownership and reduce concentration risk
    • Families planning for estate and legacy considerations

Many clients come to me after owning real estate for decades and are looking for a
thoughtful, low-pressure approach to the next phase of their investment life.