STR Law

Avoid Denied Claims: STR Insurance Essentials with Nick Massey from Proper Insurance


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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 when a guest gets injured (from cliff falls to carbon monoxide claims)

  • How LLCs, waivers, and safety measures strengthen your defense

  • The truth about umbrellas, riders, and liability limits

Nick shares real-life cases—including a $2M cliff fall, a celebrity CO poisoning, and even bat-related rabies shots—that highlight why the right insurance is non-negotiable for hosts.

🎙️ If you’re a host, investor, or property manager, this episode is a must-listen to protect your rental business, your guests, and your peace of mind.

🔗 Learn more about Proper Insurance at www.proper.insure


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STR LawBy Katie Johnson