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.

• 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.

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.

• 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.

Higher interest rates are making short-term rental deals harder to find, but that doesn't mean opportunities have disappeared. In this episode of Cash Flow Positive, Kenny Bedwell breaks down how rising borrowing costs are affecting returns, why buying now and hoping to refinance later can be risky, and how investors can protect themselves by looking beyond cash flow alone.

Kenny also explains the difference between real and fake forced appreciation, why improving a property's underlying residential value matters, and how the beginning of the year can create opportunities for investors willing to negotiate. Rather than sitting out the market because interest rates are high, learn how to evaluate individual deals, understand the risks, and adapt your strategy to the conditions in front of you.

• How rising interest rates affect returns: Even a half-percentage-point increase can significantly reduce cash-on-cash returns and turn an attractive deal into a marginal one.
• Why you shouldn't rely on refinancing: Rates may eventually fall, but there's no guarantee of when. Buying a property that only works if you can refinance soon leaves you exposed if conditions don't improve.
• Why the deal matters more than the market: Instead of ruling out entire markets because of interest rates, focus on the numbers, the property's potential, and the risks involved.
• Cash flow isn't the whole picture: A property that depends entirely on rental income can become vulnerable when revenue drops unexpectedly. Having appreciation potential and multiple exit strategies provides more flexibility.
• Real vs. fake forced appreciation: Adding expensive short-term rental amenities doesn't necessarily increase a property's underlying residential value. Improvements such as adding bathrooms, increasing liveable square footage, and upgrading kitchens can offer more durable value.
• Think about your exit before you buy: Cash-out refinancing can increase debt and reduce cash flow. Consider what happens if revenue declines or you need to sell the property.
• Use seasonality to your advantage: January and February can present negotiation opportunities on properties that have been sitting on the market, although inventory may be more limited.
• Understand cause and effect: Higher interest rates can shrink the buyer pool and leave properties on the market longer. Investors who understand these dynamics can identify opportunities instead of automatically sitting out.

Kenny Bedwell is the host of Cash Flow Positive and founder of STR Insights, a data platform for short-term rental investors. Through data-driven investing and successful short-term rentals, Kenny has replaced his W-2 income with cash flow and shares practical insights to help other investors pursue similar financial freedom.

• Want us to find the deals for you? https://strinsights.com
• Instagram: @kenny_bedwell
• YouTube: Cash Flow Positive
• LinkedIn: Kenneth Bedwell

Cash Flow Positive is an original podcast hosted by Kenny Bedwell.