VRS598 - Lessons Learned from a Disaster Scenario with Nick Massey - Proper Insurance

Vacation Rental Success

In this third week of SSTIR Crazy 2025, StayWise Rentals grapples with an insurance nightmare when a malicious pool party threatens to ruin their business.

This episode of the podcast and SSTIR Crazy Month is sponsored by Guesty your all-in-one platform for hospitality businesses to automate and optimize every aspect of your operations. ***Use code SSTIRCRAZY for 50% off your first annual plan***

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“It just makes sense to buy the best cover available," said a lone voice in a Facebook group in answer to the question “Where can I get the cheapest insurance?”.

Sadly many of the responses pointed to cut price options which is clearly the route Staywise Rentals went when they started out. And now to their horror, an incident at one of their prime beachfront homes has brought home the folly of this choice.

In this episode and third week of the SSTIR Crazy event where we follow the issues Stay Wise Rentals are facing, Nick Massey, a seasoned expert in vacation rental insurance and the director of sales at Proper Insurance, shares his thoughts on the direction they need to take.

Nick has extensive experience in identifying coverage gaps and optimizing insurance strategies for property managers, and he brings a wealth of knowledge to one of the most daunting aspects of vacation rental management. He gets right into the complexities of insurance policies, highlighting common pitfalls and actionable strategies to protect rental properties effectively.

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Are you listening to this podcast on the move? Get to the show notes here: https://www.vacationrentalformula.com/VRS598