Ep. 107 | Navigating the Short-Term Rental Landscape: Insights from Kenny Bedwell

In this Mini Breakdown, Craig Fuhr and Jack BeVier explore two major forces shaping today’s market: housing policy and artificial intelligence. They discuss President Donald Trump’s call to limit institutional ownership of single-family homes, with Craig raising concerns about long-term affordability impacts and Jack framing the proposal as largely political theater, noting that institutional buyers are currently sidelined by unfavorable financing conditions. The conversation then shifts to the rapid evolution of AI, where both highlight how dramatically more accessible and powerful AI tools have become, emphasizing their ability to boost productivity, automate tasks, and empower professionals— even those without technical backgrounds — to build and create using simple, natural-language prompts.

In this episode of Real Investor Radio, host Craig Fuhr welcomes Kenny Bedwell, founder of STR Insights, a data and advisory platform focused on short-term rental (STR) investing. Kenny shares his journey into the STR market, starting from his initial investments to developing a software that helps investors identify profitable markets and avoid regulatory pitfalls. He emphasizes the importance of data-driven decision-making in the STR space, highlighting the shift from quantity to quality in property management and the need for investors to adapt to a maturing market. Kenny discusses the current landscape of STRs, including the impact of regulations, market saturation, and the importance of understanding expenses beyond just cash flow.

In this conversation, Craig Fuhr and Jack BeVier discuss the implications of Trump's proposed $200 billion infusion into the mortgage market, exploring its potential effects on interest rates, home buyer behavior, and the overall housing market dynamics. They analyze historical parallels, market predictions, and the evolving landscape of Non-QM mortgages, emphasizing the importance of strategic pricing and quick closing in real estate transactions.

In this episode of Real Investor Radio, Craig Fuhr and Jack BeVier discuss various aspects of the current investment landscape, focusing on DSCR pricing, the influence of the five-year treasury, and the implications of recent Fed actions on liquidity. They explore the state of different asset classes, including office and multifamily properties, and provide insights into the single-family market. The conversation emphasizes the importance of being cautious and strategic in investment decisions during a time of market uncertainty.

In this conversation, Justin Spillers discusses the challenges and strategies involved in fundraising and capital raising for real estate investments. He shares insights on innovative preferred equity structures, creative marketing techniques for seller outreach, and the use of technology and AI in operations. The discussion also covers tenant screening and retention strategies, as well as the unique approach of leveraging the LIHTC strategy for value-add opportunities in real estate.

In this episode of Real Investor Radio, Craig Fuhr and Jack BeVier discuss the current state of the real estate market with guest Justin Spillers, who shares insights from his experience in multifamily investing in Ohio. The conversation covers market trends, challenges faced by investors, and the importance of effective tenant management and screening. Justin recounts his journey from law to real estate, detailing his first deal and the lessons learned along the way. The trio also delves into acquisition strategies, operational efficiencies, and the significance of building a strong team to navigate the complexities of the real estate landscape.

In this episode of Real Investor Radio, Craig Fuhr and Jack BeVier delve into the ongoing debate between single-family and multi-family real estate investments. They explore the historical context of these asset classes, the shifts in market dynamics, particularly in cap rates, and the current opportunities and risks in the multifamily market. The conversation also touches on financing strategies for multifamily investments, emphasizing the importance of understanding expense ratios and realistic cap rates. Overall, the discussion provides valuable insights for investors navigating the evolving real estate landscape.

Craig and Jack discuss how the current real estate market mirrors the early stages of 2007–2011. Pulling from firsthand experience during the Great Recession, Jack explains why he believes we’re only in the early innings of a liquidity-tightening cycle — with 2024 resembling 2007 and 2025 resembling 2008. They break down investor psychology, rate cycles, liquidity, pent-up demand, and how long real estate corrections really take to materialize. They also share practical advice for flippers and real estate investors on pricing strategy, avoiding the “loss-aversion death spiral,” and how to stay liquid to capitalize on opportunities that may appear over the next 12 months.

In this episode of Real Investor Radio, Craig Fuhr and Jack BeVier engage with Kevin Bupp, a seasoned real estate investor, discussing the current state of the multifamily market, investment strategies, and the importance of having a strong team. Kevin shares his journey in real estate, insights on mobile home park investments, and the dynamics of tenant ownership. The conversation also covers operational challenges and future growth strategies in the real estate sector.

In this conversation, Craig, Jack, and Fred delve into the evolving regulatory landscape affecting real estate investments, particularly focusing on local legislative changes and their implications. They discuss the impact of the Tenant Opportunity to Purchase Act (TOPA) in Washington, D.C., and how it has created challenges for investors. The conversation also touches on the growing scrutiny of institutional ownership in real estate and its relationship with affordability issues. Furthermore, the speakers explore the role of technology in enhancing operational efficiency and customer experience in real estate, emphasizing the importance of product quality and customer-centric approaches. Finally, they discuss the future of lending, highlighting the shifts in market dynamics and the increasing significance of risk management in the industry.