On this week's episode, Avery is joined by Ana Klein, CEO of Tax Boss, to break down how short term rental tax law can help high income earners significantly reduce their taxable income. Ana explains how strategies like cost segregation and bonus depreciation can create large paper losses that offset W2 income, while emphasizing that these benefits only work when paired with strong investments and long term planning. The conversation dives into common misconceptions, including year-one benefits, depreciation recapture, and why trying to game real estate professional status can backfire. They also highlight the importance of proper bookkeeping, time tracking for material participation, and working with qualified professionals to avoid costly IRS audits and mistakes.

How to connect with Ana:

https://www.instagram.com/taxbossana/

How to connect with Avery:

The Short Term Shop - https://theshorttermshop.com/

Short Term Shop Plus - stsplus.com

Follow us on Instagram

Follow us on TikTok

Join the Short Term Shop Facebook group

Check out the Short Term Shop on YouTube

For more information on how to get into short term rentals, read Avery’s books:

Smarter Short Term Rentals - Buy it on Amazon
Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week’s episode, Avery is joined by Dohn Thornton, a seasoned real estate investor and short sale expert who has flipped over 3,000 properties and now focuses on advanced asset protection strategies. Dohn breaks down the concept of a spendthrift trust, explaining how it differs from traditional LLCs and trusts by offering greater privacy, lawsuit protection, and potential tax advantages through a contract law structure. The conversation dives into how these trusts can shield assets from discovery, avoid triggering taxable events, and fundamentally change how investors think about income, expenses, and wealth management. Dohn also shares real world examples from his own business, including how switching to this structure deterred lawsuits entirely and reshaped his approach to investing and long-term wealth building.

How to connect with Dohn:

https://bensonfinancial.us

Instagram: @dohnthornton

How to connect with Avery:

The Short Term Shop - https://theshorttermshop.com/

Short Term Shop Plus - stsplus.com

Follow us on Instagram

Follow us on TikTok

Join the Short Term Shop Facebook group

Check out the Short Term Shop on YouTube

For more information on how to get into short term rentals, read Avery’s books:

Smarter Short Term Rentals - Buy it on Amazon
Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week’s episode, Avery is joined by Emily Tunggala. Emily shares how Hospitable is expanding beyond traditional property management software by launching a marketplace that connects property managers with owners looking for help. She explains how the platform uses performance data and insights to match the right managers with the right properties, while also giving newer managers tools to onboard clients professionally. The conversation highlights how this could change the way managers find clients, reduce time spent chasing leads, and create more opportunity based on results rather than connections.

How to connect with Emily:

https://hospitable.com/

How to connect with Avery:

The Short Term Shop - https://theshorttermshop.com/

Short Term Shop Plus - stsplus.com

Follow us on Instagram

Follow us on TikTok

Join the Short Term Shop Facebook group

Check out the Short Term Shop on YouTube

For more information on how to get into short term rentals, read Avery’s books:

Smarter Short Term Rentals - Buy it on Amazon
Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon