The STR Report's Weekend Digest - March 21st, 2026

March 21st, 2026

Good morning STR Report Community, and welcome to The STR Report’s Weekend Digest!

In today’s issue, you will find:

📱Weekend Digest: The Rental Resource Rundown

📬 See our collection of newsletters here: Prior Newsletters

☕ Good morning, STR Report Community!

Welcome back to The STR Report’s Weekend Digest — today we’re sharing another insightful podcast in our Rental Resource Rundown, diving into a topic that’s costing many hosts far more than they realize: relying on tax-driven advice instead of real performance.

Why Listening to Tax Strategists and CPA’s Will Cost You Six Figures💰🚫 

Click below to play video: 👇

🎙️ Why You Should NOT Trust Your Tax Strategist

Episode description:

Elliott Caldwell is an entrepreneur, real estate investor, and host of the Successful DNA Podcast, where he interviews business owners, founders, and professionals about entrepreneurship, investing, and building successful companies.

In this video, Elliott explains why many high-income earners, entrepreneurs, doctors, and executives are being told to buy short term rental properties and Airbnbs for tax savings, and why that advice often leads to losing thousands of dollars per month. Drawing from his experience operating hundreds of short term rental properties, Elliott breaks down the difference between tax strategy and real asset performance, explaining how cost segregation, bonus depreciation, and the short-term rental loophole actually work — and why real estate must outperform before tax benefits can create real wealth. 💸🏡

Have a question you want answered or want to be featured in the next Weekend Digest? Just reply to this email. 📬

Partner with Us!

If you have a project you’d like us to promote, or a product or service you’d like to share, please reach out to us at [email protected].

We appreciate you being a part of our STR community and for sharing our group with your business partners and associates. Thank you!