Why I Partnered with Proper Insurance to Protect My STR Business

When it comes to running a successful vacation rental business, most hosts focus on photos, pricing, and guest reviews—but what really protects your business is what happens when things go wrong.

That’s why I partnered with Proper Insurance.

Proper isn’t just another insurance company. They specialize exclusively in short-term rentals. That means they understand the unique risks hosts face—and they built a policy to actually cover them.

🎥 I Sat Down with the Proper Team – Watch Our Full Interview

I recently interviewed the team at Proper for a full YouTube deep dive on all things STR insurance.

We talked about:

  • What most hosts get wrong about insurance

  • The difference between Proper and your regular homeowners policy

  • Real-world claim stories (including my own!)

  • Why having loss of business income coverage can save your season


👉 Watch it here: Full Interview with Proper Insurance

🚨 Why I Chose Proper Insurance for Hilde Homes

I’ve been in the STR game for a while now—managing properties across Arizona and helping other hosts get their businesses off the ground. I’ve seen a lot. And unfortunately, I’ve also seen hosts think they’re covered, only to be blindsided by denied claims and fine print.

That’s why I switched to Proper.

✔️ Their policy is built for short-term rentals

✔️ They include liability, property coverage, AND loss of income

✔️ Their claims process is fast, professional, and stress-free (I’ve been through it!)

✔️ And most importantly: they actually pay out.

I share the full story of why I made the switch (and the exact moment I knew Proper was the real deal) in this short video:

🎥 Why I Chose Proper Insurance

💬 My Real-Life Water Damage Claim Experience

Earlier this year, I had over $25,000 in water damage at one of my Airbnbs—right before peak season. I was staring down $10,000 in lost bookings, plus major repairs.

Proper stepped in and handled it like pros.

  • They walked me through every step of the process

  • Communicated clearly and often

  • And covered both the property damage and the lost business income

I didn’t just recover—I came out stronger. That’s the power of the right partner.

👉 Ready to Protect Your Property?

If you’re a host, don’t wait until disaster strikes.

Get the peace of mind I have with Proper.

➡️ Click here to get a free quote

It only takes a few minutes—and could save you thousands.

John Hildebrand - Mr. Sicky