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Is Now the Right Time to Sell? Transition from Landlord to Investor

Last Updated: September 18, 2025By

Presented by JRW Investments

This is a powerful and practical discussion led by Jon Taylor of JRW Investments, one of the country’s leading voices on 1031 Exchanges and Delaware Statutory Trusts (DSTs).

With rising insurance premiums, escalating repair and property management costs, and a wave of new tenant-friendly legislation, many real estate investors are questioning whether the effort and expense of active property ownership still makes sense: Is now the right time to sell?

If you own highly appreciated investment property and are unsure of your next move, listen carefully and learn how to defer taxes, reposition capital into more passive structures, and protect your legacy — all while navigating an unpredictable economic environment. Whether you’re actively preparing to sell or simply evaluating your options, this free webinar will equip you with the strategic tools you need to make informed decisions.

DISCUSSION TOPICS INCLUDE:

  • How rising insurance costs, repair expenses, and property management fees are squeezing real estate investors’ net income
  • Why increasing regulation and shifting landlord-tenant laws are prompting many investors to reevaluate active property ownership in retirement planning
  • How a 1031 Exchange works — and why it’s about much more than just deferring capital gains taxes
  • What are Delaware Statutory Trusts (DSTs) and how are investors taking advantage of this investment vehicle
  • The IRS “rules of the road” — identification, timing, and the most common exchange mistakes to avoid
  • How to use the 1031 Exchange to transition into passive income, diversify your portfolio, or exit active management
  • Estate and tax planning benefits of DSTs and how step-up in basis works with deferred gains
  • Key criteria for selecting high-quality institutional real estate as your replacement property

GUEST SPEAKER: Jon Taylor, Registered Representative, JRW Investments

Jon Taylor, Registered Representative at JRW, is known for his consultative approach and deep expertise in the 1031 Exchange and DST marketplace. He regularly speaks at industry events and investor summits nationwide. Jon lives in Southern California with his wife and three daughters.

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