I’m Buying Long-Term Rentals Again—Here’s Why

Why would a successful short-term rental investor start buying long-term rentals again? In this episode of Cash Flow Positive, Kenny Bedwell shares why he's expanding his long-term rental portfolio, including a new quadplex under contract near Buffalo, New York, and how his investment strategy has evolved as his portfolio has grown. Kenny isn't walking away from short-term rentals. Instead, he's taking a more strategic approach to building wealth by balancing cash flow, appreciation, tax savings, and diversification. He breaks down the five reasons behind his decision, why owning more short-term rentals isn't always better, and how he's building a long-term rental portfolio with a specific exit strategy in mind. From stabilising existing properties to creating value through renovations, Kenny explains why the best investment isn't always the one generating the most cash flow today. Sometimes, it's the one positioning you for greater wealth five or ten years down the road. Key Takeaways Why diversification matters as your portfolio grows: Relying entirely on short-term rentals can expose investors to unexpected disruptions. Adding long-term rentals helps Kenny spread risk across different types of real estate investments. Cash flow builds income, but appreciation builds wealth: Kenny explains why he's taking profits from his short-term rentals and reinvesting them into properties with long-term appreciation potential rather than simply accumulating more cash flow. Quality over quantity in short-term rentals: Buying more properties isn't always the answer. Managing too many short-term rentals can become another full-time job, and spreading yourself too thin can hurt the guest experience and your returns. Why stabilising your portfolio is part of scaling: After acquiring five short-term rentals over three years, Kenny is focusing on improving operations, maintenance, amenities, and performance before expanding further. How long-term rentals fit into Kenny's tax strategy: Kenny discusses how his real estate professional status allows him to pursue tax benefits through cost segregation and depreciation on long-term rental properties, subject to the applicable tax rules. Why he's targeting properties with renovation potential: Rather than chasing immediate cash flow, Kenny is looking for undervalued properties where improvements can create genuine appreciation over a five-to-seven-year period. Building a portfolio with the exit in mind: Kenny shares his plan to acquire long-term rentals in a concentrated area near Buffalo, with the goal of potentially selling them together as a portfolio rather than individually. Why every property needs a purpose: Whether you're investing for income, tax savings, appreciation, or an eventual exit, Kenny explains why each acquisition should support a larger financial strategy. About the Host Kenny Bedwell is the host of Cash Flow Positive and founder of STR Insights, a data platform helping short-term rental investors make smarter, data-driven decisions. After replacing his W-2 income through successful short-term rental investments, Kenny has continued expanding into long-term rentals and boutique hospitality. Through the podcast, he shares his experiences, lessons learned, and strategies for building sustainable wealth through real estate. Important Links Want us to find the deals for you? https://strinsights.com STR Scale Summit: https://strscalesummit.com Instagram: @kenny_bedwell YouTube: Cash Flow Positive LinkedIn: Kenneth Bedwell Cash Flow Positive is an original podcast hosted by Kenny Bedwell.