STR Law

California probate can be slow, expensive, and messy, especially when you own rentals or run a business. In this episode, I am joined by Mark Abel, a Southern California trusts-and-estates attorney, to explain how estate planning and LLCs work together for STR owners and real estate investors. We cover why a living revocable trust is a go-to tool for avoiding probate, how a pour-over will “catch”...

Asset protection doesn’t have to be confusing, especially when you own short-term rentals.  In this episode, Katie is joined by attorney Kevin Snyder of Snyder Law to break down “layers of protection” for STR owners: insurance, LLC structuring, and when trusts may (or may not) make sense. They cover why separating properties into different LLCs can reduce risk, the real problem with “pooling” rent...

I sat down with Brett Swartz to unpack tax-smart exit planning for real estate investors and business owners—especially how a Deferred Sales Trust can help defer capital gains with more flexibility than a traditional 1031 exchange . If you’re thinking about selling, this episode is for you. Hit play, follow the show on Spotify, and share it with a friend who’s planning an exit.🎙️ #ExitPlanning #Ca...

In this episode of STR Law , attorney and real estate developer Ari Rastigar explains how zoning and entitlements shape real estate value long before construction begins. The conversation covers entitlement risk, rezoning strategies, large-scale development, 3D-printed housing, and how institutional investors approach housing in high-growth cities like Austin and Dallas. A practical discussion on...

What happens when a 90-acre Property collides with small-town politics and zoning boards? In this episode of STR Law, real estate attorney and Airbnb investor Katie Johnson sits down with Ali Haney—short-term rental owner, branding expert, and host of The Branded Market Podcast . Ali shares how she bought a 90-acre property in rural Kentucky to build a wedding venue with on-site stays, only to fac...

For this episode, our guest, Steph Weber—owner of The Weber Co, co-host at Hosted by the Webers, and partner in Cabins on the Cumberland—shares what it takes to build a sustainable short-term rental co-hosting business. Steph breaks down how branding and organic marketing helped her scale quickly, plus the lessons she learned the hard way about contracts, onboarding, client boundaries, scope clari...

When you win a lawsuit, the judgment is only as valuable as your ability to collect. In this episode of STR Law, real estate attorney Katie Johnson sits down with business litigators Mark Rossman and Noah Matthews of Rossman PC to break down what commercial collections really look like—especially when a debtor tries to dodge payment. They discuss the difference between cases where a client already...

Renovations can make—or break—your short-term rental. In this episode, real estate attorney and host Katie Johnson sits down with Minnesota investor Tanya Rooney to share a practical playbook for managing construction on STR properties.  They explain how vague scopes create chaotic bids and walk through what to include in a detailed scope (counts, locations, specs, exclusions) so proposals reflect...

Short-term rentals are booming, but financing them is where a lot of hosts get tripped up. In this episode, Katie talks with Parker, a lender licensed in 45+ states, about how STR buyers can actually qualify using traditional QM (Qualified Mortgage) loans, more flexible non-QM products (bank-statement, 1099, full-doc non-QM), and DSCR (Debt Service Coverage Ratio) loans that rely on projected STR...

Short-term rental operators can find the deals — the tricky part is bringing in investors without creating legal or partnership headaches. The questions start fast: How long is the hold? Who manages? What if someone wants out early? In this episode of STR Law, Katie Johnson sits down with Natalie Palmer (No Vacancy Podcast, Level Up Your Listing Summit) to break down a real deal she raised for an...

What if your Airbnb guest won’t leave? An overstaying guest can quickly create legal and financial headaches if you don’t know your rights. In this episode of STR Law, I’m joined by John Voss, with over 30 years representing property management companies and landlords in both residential and commercial cases. He explains the legal challenges that arise when short-term rental guests overstay, and h...

Taxes can make or break your short-term rental business, and most hosts are leaving thousands of dollars on the table.  In this episode, licensed CPA, Ryan Bakke, explains how Airbnb and vacation rental investors can use smart tax planning to keep more of what they earn. From bonus depreciation and cost segregation to entity structuring and the STR loophole, Ryan breaks down strategies in a way ev...

In this episode of STR Law, Attorney Katie Johnson sits down with Arizona realtor and attorney Mike Stone to explore his journey to real estate, property management, and short-term rental entrepreneurship. We dig into: How Mike transitioned from litigation and insurance defense to Airbnb investing The lessons learned (and money lost) from arbitrage deals — and why he now champions co-hosting Smart...

Short-term rentals are booming, but one wrong insurance move can sink your business. In this episode of STR Law , I sit down with Nick Massey from Proper Insurance—the “Lamborghini of STR insurance”—to unpack how hosts can avoid costly mistakes. We cover: Why most homeowners and landlord policies won’t protect you as a host The #1 pool and hot tub requirements you can’t ignore What really happens...

In this eye-opening episode of STR Law, attorney and Airbnb investor Katie Johnson sits down with short-term rental safety expert Justin Ford of Breezeway to break down what may be the largest jury verdict ever involving a short-term rental — a staggering $11.6 million. We dig deep into the case details: The incident that led to a guest’s life-changing injury The safety oversights and legal misste...

Are you confident about your lake access rights? Do you really know where your property line ends? In this episode of STR Law , real estate attorney Adam Toosley of Thompson Coburn LLP joins us to demystify some of the most misunderstood—and litigated—aspects of property ownership. With over 20 years of real estate litigation experience, Adam explains key legal concepts like adverse possession, ea...

Thinking about buying a short-term rental in a neighborhood with a Homeowners Association (HOA)? You need to listen to this first. In this episode of STR Law , we sit down with one of the nation’s top HOA attorneys, Kevin Hirzel of Hirzel Law, PLC, to break down everything short-term rental (STR) investors must know before purchasing property in an HOA-governed community. We dive deep into: ✔️ The...

Katie brings land-use litigator Kyle Konwinski onto STR Law to unpack the blockbuster lawsuit that forced the City of Northville, Michigan, to reopen its two main downtown streets—just in time for local businesses to survive the summer. Spoiler: Kyle’s clients won. In this episode you’ll learn: How COVID-era “temporary” street closures morphed into a permanent May-through-November shutdown that gu...

In this powerful first episode of STR Law , real estate attorney and Airbnb investor Katie Johnson sits down with Sarah Glidewell from the Karwells to unpack the two-year legal odyssey that nearly shut down her Cadillac, Michigan short-term rental, colloquially known as "Orange Cadillac." From city lawsuits and zoning nightmares to grassroots campaigns and a bold pivot to podcasting, Sar...

🎙️ Episode 2: The Guest Who Wouldn’t Leave — How to Handle Airbnb Evictions, Nightmare Guests, and Legal Loopholes What do you do when your Airbnb guest refuses to leave? In this episode of STR Law , I sit down with Tony Stancato, Michigan short-term rental host, investor, and property manager, to unpack a real eviction horror story that every host needs to hear. From a guest who falsely claimed a...

Katie is joined by STR Insights founder Kenny Bedwell to break down the real impact of short-term rental regulations. Learn how to spot STR-friendly markets, avoid risky “unregulated” zones, and why community sentiment matters. From zoning maps and resale strategies to pricing hacks and market research, this episode is packed with real talk for serious Airbnb investors. Subscribe now—smart hosts d...