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RealDealChat / Lessons from Real Estate InvestorsYour Gateway to Real Estate Investing Success Author: RealDealCrew Jack Hoss
RealDealChat brings you unfiltered conversations with elite real estate investors who share their journey to success. Each episode delivers practical wisdom from industry leaders who openly discuss: Proven strategies that are generating results in today's market Honest reflections on mistakes and missteps they've encountered along the way Actionable takeaways you can implement immediately to elevate your real estate portfolio Whether you're a seasoned investor or just starting out, our no-fluff interviews provide the real-world insights you need to navigate the complexities of real estate investing and accelerate your path to financial freedom. Join us as we decode the secrets of successful real estate investors and help you transform their hard-earned lessons into your competitive advantage. Language: en Genres: Business, Education, How To, Investing Contact email: Get it Feed URL: Get it iTunes ID: Get it |
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Short-Term Rentals Aren’t Easy Anymore—Here’s What Still Works with Kenny Bedwell
Episode 808
Tuesday, 17 February, 2026
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 reshaped the landscape, and why data—not hype—must drive every STR decision today.This conversation covers how Kenny uses nationwide data to identify high-ROI markets most investors overlook, why regulated markets can still outperform, how to self-manage STRs without burning out, and what amenities and design choices actually move the revenue needle. Kenny also shares his most expensive mistakes, why parking and neighbors matter more than Instagram aesthetics, and how to think about guest avatars instead of generic “travelers.”If you’re considering short-term rentals—or already in the game and feeling squeezed—this episode will reset your expectations and sharpen your strategy.🌐 Learn more about Kenny & STR Insights: 👉 https://strinsights.com📸 Follow Kenny on Instagram: 👉 @kenny_bedwellIf this episode helped you think more clearly about short-term rentals, share it with one investor friend—and learn more at https://realdealcrew.comKeywords: short term rental investing, Kenny Bedwell, Airbnb investing, STR data analysis, vacation rental investing, short term rental mistakes, Airbnb competition, STR market analysis, self managing short term rentals, real estate data investing, STR regulation, RealDealChat podcastWork With RealDealCrewIf you’re already closing deals but your intake, follow-up, or visibility feels inconsistent, here are two ways to go deeper:Take the Deal Intake AssessmentSee how resilient your current operation actually is.→ https://assessment.realdealcrew.comBook a Fit CallIf you want to explore what a fully system-driven deal flow looks like, let’s talk.→ https://realdealcrew.com/bookLIKE • SHARE • JOIN • REVIEWWebsiteApple PodcastsYouTubeYouTube MusicSpotify
