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Real Estate Without the Headaches: DSTs for Pilots

Real Estate Without the Headaches: DSTs for Pilots

Update: 2025-09-15
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Description

You've probably heard the saying, "The best day of your life is when you sell it": and no, we're not talking about boats. We're talking about self managed rental properties. In this episode, Tim is joined by Trevor Flor, Navy veteran, former Delta pilot, and now a real estate investment advisor specializing in DSTs (Delaware Statutory Trusts) and 1031 exchanges at Aimpoint Investments. Trevor breaks down how 1031 exchanges really work, why DSTs were created, and how this is one potential approach to consider.

What You'll Learn from This Episode

  • 1031 Exchanges Demystified: How selling investment property can be one potential approach to consider, depending on individual circumstances.
  • DSTs as a Solution: Why Delaware Statutory Trusts were created, how they enable fractional ownership, and when they work best.
  • Three DST Strategies: Using DSTs as a primary, backup, or complementary approach depending on your goals and exchange value.
  • Timeline Rules That Matter: The 45-day identification window and 180-day close deadline - and what happens if you miss them.
  • Partial Exchanges and Cash Boot: Can you peel off cash from a sale and still do a 1031? Yes, but at what cost?
  • Accredited Investor Requirements: What qualifies you for DST access and what documentation you'll need.
  • Types of DST Properties: From multifamily and industrial to storage, hotels, and more - what's available and how it's selected.

Resources:

Trevor Flor’s firm, Aimpoint Investments: www.aimpointinvest.com
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Send Us Your Questions: info@pilotsportfolio.com

This episode is sponsored by: Beacon Relocation

Beacon Relocation is a real estate firm helping pilots and air traffic controllers save money on their real estate transactions. By tapping into their network of over 1500 real estate agents across the country, pilots can save 20% of the real estate agent’s commission towards your closing cost on the sale or purchase of your home. Visit https://www.beaconrelocation.com/ to learn more. 

Timothy P. Pope is a Certified Financial Planner™and principal owner of 360 Aviation Advisors, LLC (“360 Aviation Advisors”), a registered investment advisory firm. Investment advisory services are provided through 360 Aviation Advisors, in its separate and individual capacity as a registered investment adviser. Podcast episodes are provided through Pilot’s Portfolio, in its separate and individual capacity.

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Real Estate Without the Headaches: DSTs for Pilots

Real Estate Without the Headaches: DSTs for Pilots

Timothy P. Pope, CFP®