Cash Flow Positive Part 2: Recent Hard Lessons Learned
Are you truly ready to launch your next short-term rental—or are you overlooking the hidden costs that could derail your returns?
In this episode of Cash Flow Positive, Kenny Bedwell continues the conversation on hard-earned lessons from the field, offering raw and practical advice every STR investor should hear. This isn’t just theory—it’s a behind-the-scenes look at what really happens when properties take longer to launch, when holding costs spiral, and when “almost guest-ready” just isn’t good enough.
Drawing from his own projects, Kenny breaks down what many investors miss when budgeting for renovations, managing out-of-state setups, and relying too heavily on contractors without local oversight. He also digs deep into market conditions, sharing what he’s seeing as the industry matures, where opportunity still lies, and why having a “moat” around your investment is more crucial than ever.
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 having boots on the ground can make or break your STR setup
- What it really takes to get a property fully guest-ready—not just 90% there
- How to build a “moat” around your STR and avoid constant reinvestment battles
- When seller credits work—and when they’re just smoke and mirrors
- How to prepare for appraisal gaps and navigate unrealistic seller expectations
- Why you should test everything—including toilets and outlets—before launching
- What STR investors often overlook when assessing resale value
- How to avoid getting lured into overpriced “super properties”
- Why now might be a better time to buy than later this year
- What maturing markets mean for buyers, sellers, and long-term investors
- And much more...
Resources:
Connect with Kenny on LinkedIn
Part 1: Types of STR Markets No One is Talking About