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August 14, 2025 29 mins

This week, Scott sits down with Jason Watson from WCG CPAs and Advisors to talk about the top 3 mistakes high-income pilots should avoid when investing in rental properties. As pilots and other high earners look for ways to diversify their income beyond their primary careers, rental properties offer a powerful path to building lasting wealth- if you approach it the right way.

Here’s some of what we discuss in this episode:

🛫 Why pilots’ schedules make rentals a uniquely attractive investment

📉 The #1 misconception about rentals as a tax-saving strategy

🏠 Short-term rental loophole explained and how to qualify

💰 Using cost segregation and bonus depreciation to your advantage

📋 Which personality types make the best landlords

Resources for this episode:

Get Jason’s book, I Just Got a Rental, What Do I Do?

https://www.amazon.com/Just-Got-Rental-What-Considerations/dp/B0DJBY6ZQ3

WCG CPAs and Advisors 

https://wcginc.com/

Resources:

Our website: https://retireairlines.com/

Phone: (419) 314-4139

Contact our team: https://retireairlines.com/contact-us/

Schedule an introductory call: http://callosborn.com/

Order your no-cost retirement toolkit: https://keap.page/lde199/the-pilot-s-planner-toolkit.html

Check out our other no-cost financial resources & guides here: https://retireairlines.com/guides-whitepapers/

The “When I Die” binder: https://retireairlines.com/wp-content/uploads/2024/10/Scott-O-FILLABLE-BINDER-10.22.24-1.pdf

Watch the podcast on YouTube: https://www.youtube.com/channel/UC_hNGqqVjqgtuoYZlu9i4yQ

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