Insurance
Ted McGlone
Ross Stewart
Hi Ted
We insure with Proper Insurance. While more expensive they provide excellent coverage for short term rentals.
Ross
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Ted McGlone
Ross Stewart
Curious who you had a commercial policy through? I believe they are only offered by Proper and CBIZ. Unless you had a commercial business policy with off premises coverage it does not have the same benefits.
You are correct. They are more expensive. I spent my carrier working as a private investigator and saw all kinds of claims many with enormous payouts and want to make sure we are fully covered.
I guess get whatever coverage you are comfortable with.
What Proper Covers That Traditional Policies Typically Do Not (or Limit Heavily)
- Unlimited (or high-limit) guest damage without sub-limits that cap payouts.
- Off-premises incidents tied to your rental (e.g., a guest injured on a bike you provided or at a nearby beach).
- Full business income protection based on your actual bookings, not market averages.
- STR-specific perils like bed bugs, squatters, liquor left by guests, privacy violations (e.g., cleaner walking in), and amenity-related claims.
- No business activity exclusion — coverage holds even during frequent rentals or vacancies.
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Julie Cashin -759
I recently learned that my RLI policy will not be renewed in August. My agent contacted RLI and received the following response:
"Unfortunately, due to the AOAO's procedures regarding how claims are handled, we will not be able to reconsider coverage for this condo."
Since my agent does not represent other insurance companies, I now need to find a new agent and carrier.
If you've had a good experience with an insurance company or agent that understands Whaler units, vacation rentals, and condo ownership, I would really appreciate any recommendations.
I know there were a few other owners with RLI coverage who were non-renewed earlier this year, so I'm especially interested in hearing what companies they ended up using.
Thanks in advance for any suggestions!
Julie Cashin
Ross Fernandes
Sent: Wednesday, June 17, 2026 2:47 PM
To: WhalerOwners <whaler...@googlegroups.com>
Subject: [Whaler Owners] Re: Insurance
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Keith Paulsen Whaler Maui
Jenny Babcock?
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Comparion Insurance Agency
A Liberty Mutual Company
Direct: 808-913-6102 | Fax: 603-242-1833
Sent: Wednesday, June 17, 2026 2:47 PM
To: WhalerOwners <whaler...@googlegroups.com>
Subject: [Whaler Owners] Re: Insurance
mike feeney
Keith
I sent an email to you. Did you get it?
Mike Feeney 559