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How I Turned a $1,000,000 Tax Bill Into $200,000 by Investing in Airbnbs
In 2025 I made $2.85M and should have owed $1M in taxes. I paid about $200K. Here's how 8 Airbnbs and $2M in depreciation changed everything.
7 min read


Quiet Your Mind, Build Your Vision
Why visionaries need silence, not more hustle. Elliott Caldwell shares his real, unfiltered take on protecting quiet time, killing bad habits, and building a team that gives you the freedom to think clearly.
6 min read


We’ve Outgrown Our Name: Home Team is Now The Rise Collective
Two and a half years ago, Michael and I started with a bold mission: to become the first and only vacation rental management company that could perform nationwide. That vision became Home Team Luxury Rentals. Fast forward to today, and that dream has multiplied. What started with managing a few properties has evolved into a national portfolio of more than 400 luxury vacation rentals and the creation of several thriving, vertically integrated companies. Our management company
3 min read


TRUMP'S BIG BEAUTIFUL TAX BILL // The 2025 Tax Plan That Could Make or Break Real Estate Investors
Watch on YouTube: https://www.youtube.com/watch?v=eI8w3oTXYg4 The 2025 tax plan could save you tens of thousands... or cost you big if you’re not prepared. In this video, I break down Trump’s proposed tax overhaul and what it means for real estate investors, especially if you’re using strategies like bonus depreciation and the STR loophole. Whether you’re a W-2 earner, business owner, or full-time investor, this video covers: ✅ The return of 100% bonus depreciation ✅ Short-te
1 min read


Elliott Caldwell’s 2026 Investment Playbook
Resort-Style Short-Term Rentals Built for Control, Cash Flow, and Long-Term Relevance A Clear Framework for the Next Phase of Short-Term Rentals The short-term rental industry has matured. Generic Airbnbs, copy-paste properties, and thin margins are becoming increasingly fragile as competition and regulation rise. This page is a brief overview of the investment framework outlined in Elliott Caldwell’s 2026 Investment Playbook—a control-first strategy focused on large, resor
1 min read
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