Cash Flow Positive

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.

Interest Rates Are High. Should You Still Buy Short-Term Rentals? 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. Key Takeaways 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. About the Host 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. Important Links 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.

I Bought a 14-Room Hotel: What I Wasn't Prepared For Kenny Bedwell finally has his 14-room boutique hotel in downtown New Orleans open to guests. But getting there was anything but simple. In this episode of Cash Flow Positive, Kenny pulls back the curtain on the project and shares the challenges, mistakes, delays, and unexpected lessons that came with buying and renovating a historic hotel in the Treme district, right across from the French Quarter. From navigating city permits and historic requirements to managing contractors, construction delays, holding costs, hotel operations, Wi-Fi infrastructure, guest safety, and the realities of running a property with staff, Kenny explains what he wasn't prepared for and what he would do differently next time. Key Takeaways What it was really like buying and renovating a 14-room boutique hotel for $1.495 million and investing roughly $900,000 into the project. Why city permitting can become one of the biggest delays in a renovation project, particularly in historic areas. Why you can't completely hand off responsibility to your contractor. The person who cares most about the project is ultimately the person paying for it. How disconnected permitting and inspection processes created unexpected delays and additional work. Why you need to understand the entire approval process before construction begins, including what happens after the renovation is supposedly finished. The contractor lesson Kenny learned about incentives and deadlines, especially during the final stages of a large project. Why construction draw schedules can create an incentive problem when contractors have already received most of their payment but still have work left to finish. How bonuses and penalties could help keep contractors motivated and why Kenny plans to build clearer incentives into future renovation agreements. Why holding costs matter so much when a property isn't generating revenue yet. Kenny explains that the hotel was costing roughly $5,000 per week during the project. Why contracts need clear expectations, deadlines, responsibilities, and consequences before work begins. Why unexpected problems are inevitable during major renovations, especially when working on an old building. The importance of having both financial and mental preparation for construction surprises. Why a hotel is a completely different operational beast from a typical short-term rental. How a 14-room hotel can have more than 200 connected devices, making reliable Wi-Fi and connectivity critical to the guest experience and daily operation. Why hotel operations require much more planning and hands-on management, from staff and payroll to guest interactions and safety procedures. Why hotel guests and reviews create a different marketing challenge compared with operating an individual Airbnb. How hotel regulations can introduce requirements that STR investors may never encounter, including specific electrical and safety restrictions. Why anyone considering buying a hotel should study how to actually operate one, not just focus on the acquisition and potential revenue. The personal sacrifices involved in completing a major project, including Kenny's regular trips to New Orleans and the impact on his family and personal life. What Kenny learned about working with contractors, investors, partners, city officials, and local relationships. Why the project became a major personal growth experience, even beyond the financial and portfolio implications. The people who helped Kenny get the hotel across the finish line and why he credits the team rather than treating it as a solo accomplishment. About the Host Kenny Bedwell is the host of Cash Flow Positive and an experienced short-term rental investor. Through the podcast, Kenny shares practical insights on real estate investing, short-term rentals, market data, cash flow, and the lessons he's learned from building and operating his own portfolio. Important Links La Corte Hotel: Check out Kenny's 14-room boutique hotel in New Orleans. https://lacortehotel.com STR Insights: 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.

How Much Cash Do You Really Need to Buy an STR? How much cash do you actually need to buy a short-term rental? It’s a question Kenny Bedwell gets all the time, and the answer has changed dramatically as the STR industry has become more competitive. In this episode of Cash Flow Positive, Kenny breaks down what it really takes to invest in a short-term rental today, why STRs have become a much more capital-intensive investment, and why having more money doesn't automatically mean you'll get better returns. From the five major components of an STR investment to the point where additional spending starts producing diminishing returns, Kenny explains how investors can think more logically about the amount of capital they put into a property. Key Takeaways Why STR investing has become a luxury-style investment that requires significantly more upfront capital than it did several years ago. The five things you need to budget for: down payment, closing costs, improvements, amenities, and furnishings. How the STR industry has changed since 2016, from relatively simple Airbnb setups to highly designed, amenity-driven properties. Why the rise in competition has increased the amount investors need to put into their properties to achieve strong returns. Why outdated STR advice can be misleading as the industry continues to evolve and professionalise. How different markets are at different stages of adoption and why that affects the level of investment required to compete. Why there isn't a secret market where you can invest almost nothing and still expect a great return. Kenny's personal benchmark of roughly $150,000 in available capital as a minimum starting point for investing seriously in an STR today. Why having around $200,000 can open up more options and make it easier to properly fund a property. Why roughly $300,000–$350,000 in available capital can create a different level of opportunity, particularly when competing for larger properties and better amenities. Why more capital doesn't mean you should spend all of it. Kenny explains how diminishing returns eventually kick in. The danger of overspending on design, furnishings, amenities, or expensive vendors simply because you have the money available. Why gross revenue can be a vanity metric and why investors need to look at what they're actually netting relative to the capital invested. Why occupancy isn't everything. Kenny shares an example of a property producing strong net income despite having only 46% occupancy. The difference between being fully booked and actually generating a strong ROI. Why investors need to find the balance between underinvesting and overspending. How to use the competition in your market to understand what level of investment is actually required. Why the goal isn't necessarily to create the most expensive property, but to create a property that produces a strong return on the capital invested. About the Host Kenny Bedwell is the host of Cash Flow Positive and an experienced short-term rental investor. Through the podcast, Kenny shares practical insights on real estate investing, short-term rentals, market data, cash flow, and the lessons he's learned from building and operating his own portfolio. Important Links STR Insights: 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.

Stop Asking Me What the Best STR Markets Are “What are the best markets to invest in?” It’s one of the most common questions Kenny Bedwell gets asked. But as the short-term rental industry has become more professional and competitive, that question has become much harder to answer. In this episode of Cash Flow Positive, Kenny explains why there is no single list of “best markets” that works for every investor. The right market depends on how much you can actually invest, what you're trying to achieve, and what type of market you're willing to operate in. Kenny breaks down how the professionalisation of the STR industry has changed the way investors should evaluate markets, why your budget can determine where you can realistically compete, and why personal preferences matter more than investors might think. Key Takeaways Why “What are the best markets?” is becoming the wrong question as the STR industry becomes more competitive and professionalised. How the STR market has evolved from simply choosing a popular market to identifying the right property and sub-market within it. Why your investment budget can determine which markets make sense for you. The five components of an STR budget: down payment, closing costs, improvements, amenities, and furnishings. Why stretching your budget can quickly become a problem when unexpected project costs start adding up. How diminishing returns can affect heavily invested properties and why spending more doesn't automatically mean earning a better return. Why you need enough capital to compete with the existing top properties in the market you're entering. How to research what competitors are actually spending by looking at newly launched properties, their amenities, design, furnishings, and overall level of investment. Why today's investment costs matter rather than relying on what properties may have cost before or during the COVID-era STR boom. Why your investment goals need to be specific, whether that's cash flow, cash-on-cash return, tax savings, or long-term wealth. Why “I want as much as possible” isn't a useful investment goal and how establishing a minimum acceptable return can make decisions clearer. Why your personal preferences matter when choosing a market. How personal biases about certain locations can cause investors to overlook opportunities. Why you need to be interested enough in a market to operate the property well, even if you're primarily investing for the numbers. Why the average property isn't necessarily the target when you're looking for strong STR returns. How defining your budget, goals, and preferences together can narrow down the markets that actually make sense for you. The three questions investors should ask instead: What's my budget? What are my ROI goals? What are my personal preferences? About the Host Kenny Bedwell is the host of Cash Flow Positive and an experienced short-term rental investor. Through the podcast, Kenny shares practical insights on real estate investing, short-term rentals, market data, cash flow, and the lessons he's learned from building and operating his own portfolio. Important Links STR Insights: 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.