Should You Buy a Rental Property in 2026?

I Bought a Rental with a Flooded Basement.

What happens when you’re about to close on a rental property… and the basement is full of water? In this episode of Be a Better Landlord, Ashley Kehr shares the story of an off-market rental property deal that hit a major closing-day problem: a failed sump pump, a flooded basement, and damaged mechanicals. Instead of walking away immediately, she worked through her options with her attorney, contractors, and the seller to negotiate a seller credit and keep the deal moving. You’ll hear why the final walkthrough matters, how escrow and seller credits can help solve surprise problems, and why real estate investors need to stay calm when a deal gets messy. Subscribe for more real estate investing stories, landlord tips, and lessons from the field.

Insurance Companies Will Pay Landlords for Monthly Rentals — Here’s How to Get In

In this episode of Be a Better Landlord, Ashley Kerr sits down with Abi Horton, founder of Aros, to talk about one of the biggest overlooked opportunities for landlords: midterm rentals. Abi breaks down what midterm rentals are, how they differ from short-term and long-term rentals, and why monthly rentals are becoming more important for landlords in 2026. She explains how relocation companies, traveling professionals, and insurance displacement housing create opportunities for landlords to fill vacancies with longer, more stable bookings. Whether you own a long-term rental, short-term rental, or vacant property, this episode will help you understand how midterm rentals could become a powerful part of your rental strategy. Learn more about Abi Horton and Aros: Website: www.stayarros.com Instagram: @theabihorton

How Scott McGillivray Turned One Student Rental Into a Real Estate Empire

In this episode of Be a Better Landlord, host Ashley Kehr sits down with Scott McGillivray, longtime HGTV star, award-winning executive producer, real estate investor, contractor, entrepreneur, and educator. Best known for shows like Income Property, Moving the McGillivrays, Buyers Bootcamp, Scott’s Vacation House Rules, and Renovation Resort, Scott shares how he went from a broke university student to building a real estate portfolio across North America. Scott breaks down the story of buying his first rental property using a student loan, why cash flow matters more than “location, location, location,” how leverage can increase returns, and why the right tools are essential for analyzing rental properties in today’s market. He also shares hard-earned lessons from bad tenants, late-night toilet plunging, contractor problems, fires, market crashes, and even accidentally buying 33 houses in Cleveland. Whether you’re buying your first rental, scaling from five properties to ten, or trying to become a better landlord, this conversation is packed with practical advice on cash flow, financing, portfolio optimization, and getting rich slowly through real estate. Learn more about Scott McGillivray: Hootsuite: hootbio.com/scott_mcgillivray Website: scottmcgillivray.com Instagram: instagram.com/scott_mcgillivray Facebook: facebook.com/EverythingScottMcgillivray TikTok: tiktok.com/@scott_mcgillivray

3 Ways to Buy a Rental Property in 2026 (Even If You’re Broke)

Want to buy a rental property in 2026 but don’t have a ton of cash? In this video, Ashley Kehr breaks down 3 proven strategies investors are using right now to fund their first (or next) deal from traditional down payments to assumable mortgages and seller financing. If you’ve been stuck waiting for the “perfect time” or the “perfect deal,” this is how you actually get started. Follow Ashley Kehr: Instagram: https://www.instagram.com/wealthfromrentals YouTube: https://www.youtube.com/@WealthFromRentals

Should You Buy a Rental Property in 2026?

Should you buy a rental property in 2026 or wait it out? In this episode of Be A Better Landlord, Ashley Kehr sits down with Tony J. Robinson to break down what’s actually working in today’s market. From short-term rentals to long-term strategies (and even renting by the room), we cover how smart investors are adapting to higher rates, tighter regulations, and shifting demand. If you’re wondering whether 2026 is a good time to invest or where to even start this is the clarity you’ve been looking for. Want more STR strategies and real-world investing advice? Follow Tony here: Instagram: @tonyjrobinson Listen to the Real Estate Rookie Podcast (BiggerPockets)