What does it really take to launch a short-term rental successfully—when things don’t go as planned? In this solo episode of Cash Flow Positive, Kenny Bedwell pulls back the curtain on two recent STR setup experiences that tested his patience, budget, and systems.

Kenneth shares everything he learned while launching properties in Asheville and Kentucky, including working with designers, managing contractors, and navigating delays, disasters, and unexpected design decisions. One project turned into a complete nightmare, with miscommunications, missed deadlines, and a designer who ghosted him in the middle of the process. The other? A more streamlined—but still challenging—process that highlighted the value of clear communication, strong referrals, and aligned teams.

If you’ve ever thought about hiring a designer or project manager to help launch an STR—or wondered what pitfalls to avoid—this episode delivers a firsthand look at what not to do and what you can do instead to protect your investment and timeline.

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 hiring a designer isn’t enough—and what you actually need them to do
• How to avoid costly delays when setting up a short-term rental
• The one mistake that caused a project to go totally off the rails
• Why referrals and vetting are non-negotiable for anyone on your team
• What happens when designers and contractors aren’t in sync
• How small miscommunications lead to big issues (and how to fix them)
• The lessons learned from a 10,000 sq ft STR project in Kentucky
• Why some STR entrepreneurs are choosing in-house design and build teams
• And much more...

Resources:

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