Should You Sell an Underperforming STR?

21/07/2025 10 min

Listen "Should You Sell an Underperforming STR?"

Episode Synopsis

Ready to save $10k-$50k in taxes this year? https://taxstrategy365.com/yt-appIs it time to sell your underperforming short-term rental? Or should you keep holding?Most investors only look at cash-on-cash return. But return on equity? That’s where the real money is made. In this video, I’ll show you exactly how to calculate it — and how to decide whether to sell, refinance, or hold your STR for long-term growth.Watch until the end if you want to:✅ Understand the #1 mistake investors make when holding too long✅ Learn why an 8-year breakeven is your tipping point✅ See how to triple your portfolio with strategic exits✅ Get my personal framework for deciding when to redeploy your capital✅ Avoid the momentum-killing trap most investors fall into when they sellWhether you’re investing for cash flow or appreciation, this one decision can change the entire trajectory of your real estate portfolio. Run the numbers — then move with confidence.Timestamps:00:00 Why this one metric can change your entire investing strategy01:00 Cash-on-cash return explained (and when it fails you)02:00 The problem with rising equity and flat cash flow03:30 Return on equity math breakdown04:30 Why some properties lose money but make millionaires06:00 Cash flow investor vs appreciation investor08:00 When it’s time to sell — and when it’s a huge mistake09:00 How to exit without losing momentum10:00 Should you sell an underperforming STR?Let's connect!► Instagram: https://www.instagram.com/ryanbakkecpa/► LinkedIn: https://www.linkedin.com/in/learnlikeacpa/► Twitter: https://x.com/RyanBakkeCPA► Facebook: https://www.facebook.com/ryanbakkecpa► TikTok: https://www.tiktok.com/@ryanbakkecpa*None of this is meant to be specific investment advice, it's for entertainment purposes only.