What do you do when a property isn’t performing—and how do you know if it’s time to cut your losses or hold tight and turn it around?
In today’s episode of the Cash Flow Positive Podcast, Kenny Bedwell offers a grounded, practical perspective on one of the toughest situations a real estate investor can face: owning a short-term rental that just isn’t working. Drawing from real-world examples and lessons learned from clients across the U.S., Kenny walks through the key questions to ask before rushing to sell, and the most common (and fixable) issues holding properties back.
You’ll learn why immediate selling is often premature, how to calculate the true value of tax savings and appreciation, and what steps to take to improve revenue without over-investing. Whether you're breaking even, losing a little, or just frustrated with underperformance, this episode is packed with insight to help you analyze, adjust, and move forward with confidence.
If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!
In This Episode You'll Learn:
- Why not all underperforming properties are “bad” investments
- How to avoid locking in unnecessary losses by selling too soon
- What to analyze before deciding to exit a property
- Why tax savings, equity paydown, and appreciation still matter
- The top 3 levers to increase STR revenue—and how to check them
- How to remove personal bias and get honest feedback on your property
- When it does make sense to sell—and how to do it strategically
- What seasoned investors know about failure and learning from mistakes
- And much more...
Resources:
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