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The short-term rental loophole offers incredible tax-saving opportunities but requires careful market research and property selection to be profitable in today's competitive landscape. While the tax incentives can be life-changing, many Airbnbs have become money pits due to changing market conditions and lack of proper analysis.

Take our free Tax Planning Checklist & learn about what tax savings may be available for you in our minicourse at https://taxplanningchecklist.com

At the very least, get on our newsletter to gain access to free live events and exclusive insight you won't find anywhere else: https://www.prosperlcpa.com/subscribe

Get in touch with John at: https://johnbianchi.mykajabi.com/

Make Sure You Checkout Our Other Resources on the STR Loophole!!!

What is the Short-Term Rental Loophole?

Dangers of the Short-Term Rental Loophole
What the One Big Beautiful Bill Means for Short Term Rental Investors

• Most investors make critical mistakes by not using data tools like AirDNA or misinterpreting the data
• Focus on full-time hosts with 270+ days of availability and multiple recent reviews for accurate revenue projections
• Use the "20% rule" to quickly assess market potential (revenue should be 20% of purchase price)
• Study successful properties in your target market to identify revenue drivers and build a "buy box"
• Cash flow should be prioritized over tax benefits to ensure long-term sustainability
• Avoid oversaturated "Class A" vacation markets where property values have increased beyond revenue potential
• Expect 8-20% cash-on-cash returns from well-selected properties
• Setting up an STR requires significant initial effort but becomes much easier with proper systems
• Choose markets with established regulations to avoid future compliance issues
To learn more about selecting profitable short-term rentals, visit strsearch.com for free educational resources or to schedule a consultation.

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Chapters

1. Introduction to STR tax advantages (00:00:00)

2. Common pitfalls in STR investing (00:04:16)

3. Finding profitable markets with the 20% rule (00:10:44)

4. Cash flow vs tax benefits (00:18:13)

5. Property selection and ROI expectations (00:28:57)

6. Is STR investing worth the effort? (00:38:28)

127 episodes