STR Investing 101: The High-Income Professional’s Guide to Wealth with Airbnbs

In this episode of Assets and Orthopedics, I break down one of the most misunderstood and most powerful tax strategies available to high-income professionals: the short-term rental loophole. If you're making great money but feel crushed by taxes, this episode is your roadmap to reclaiming control, buying back your time, and building long-term wealth.

I also reveal how I use this exact strategy in my own Airbnb portfolio and why 100% bonus depreciation in 2025 is a game-changer.

🔑 What You’ll Learn:

• How short-term rentals legally offset W-2 and 1099 income
  
  
• Why you don’t need real estate professional status (REPS)
  
  
• What 100% bonus depreciation means and how to use it
  
  
• Real-world numbers: $600K property = up to $80K in tax savings
  
  
• My personal Airbnb story. What worked, what didn’t
  
  
• How to automate short-term rentals (even while working full-time)
  
  
• Tools, systems, and the one app that changed the game for me
  
  
• A bonus strategy: combining infinite banking with Airbnb investing
  
  
• Why physicians need to stop playing defense with taxes
  
  

⏱ Timestamps:
 00:00 – What is the STR tax loophole & how it work?
 03:00 – Why this applies to W-2 earners (not just full-time investors)
 05:00 – What bonus depreciation is and why 2025 is the year to act
 07:00 – Real numbers from my first $600K property
 09:00 – My STR journey: Charleston to Indianapolis
 12:00 – You don’t need a beach house. just demand & systems
 14:00 – Why systems = freedom (even as a busy physician)
 15:00 – Automation tools: Turno, Gusty, PriceLabs, and more
 18:00 – How to qualify for material participation
 21:00 – The 1-property-per-year playbook
 22:00 – BONUS: Infinite banking + STR = 2X wealth growth
 24:00 – Final recap and next steps
 25:40 – LegacyRx Conference announcement

💥 About Dr. Kyle Stephenson:
I’m Dr. Kyle Stephenson, an orthopedic surgeon, real estate investor, and founder of Assets and Orthopedics. My mission is to help physicians escape the grind, reclaim their time, and build intentional wealth through real estate, mindset, and elite financial strategies.

📲 Get Connected:
 📩 DM me “short-term rental” on Instagram for the step-by-step guide
 🎟 LegacyRx Conference: https://legacyrxconference.com
📘 Want to learn about infinite banking? Message me “banking” to get resources
🌐 More at Joinlegacyrx.com

⚡ Like, Subscribe & Share
If this episode helped you think like the wealthy. Drop a comment, hit subscribe, and send it to a colleague tired of paying six figures in taxes.

🌐 Connect with Dr. Kyle Stephenson on social media to stay updated on expert insights and strategies, and schedule your personalized consultation today to start building your path to financial freedom:

🔍 Instagram: @dr.kylestephenson
🔍 LinkedIn: Kyle Stephenson, D.O.
🔍 Facebook: Kyle Stephenson
🔍 Website: www.joinlegacyrx.com
🔍 Schedule a call & access resources: https://linktr.ee/kylestephenson

Network and Learn with Millionaires and Industry Leaders this October 24-25, 2025 → https://link.joinlegacyrx.com/widget/form/SZpeggmkXmXlDWnGtO9Ilink.joinlegacyrx.com

If you want to learn more about Infinite Banking Concept, click below: http://beyourownbank.com/ks

Don't miss out on the opportunity to transform your financial future. Subscribe now and start your journey towards financial wellness with Dr. Kyle Stephenson! 💼