Short-Term Rentals Aren’t Easy Anymore—Here’s What Still Works with Kenny Bedwell

Real Estate Investing with RealDealCrew · Feb 17, 2026 · 46m

Kenny Bedwell explains why short-term rentals are harder today—and how data, design, and discipline still create outsized returns.

In this episode of RealDealChat, Kenny Bedwell—short-term rental investor, former Citibank data analyst, and founder of STR Insights—breaks down what has actually changed in the Airbnb market over the last eight years.

Kenny shares his journey from house hacking a duplex in Buffalo to owning short-term rentals across multiple states and even operating a hotel. We dive into why the “throw it on Airbnb and print money” era is over, how competition and regulation…