Underlying property policies
Whether the underlying property policies actually contemplate short-term rental use, or exclude it and have not been read closely
Short-term rental is the segment where the coverage question and the legality question cannot be separated. A homeowners or dwelling fire policy excludes the commercial use. Platform host protection is not your insurance program and was never designed to be. And in New York City, registration status under Local Law 18 can determine whether a carrier treats a loss as a covered occurrence at all.
Start the ReviewWhether the underlying property policies actually contemplate short-term rental use, or exclude it and have not been read closely
What platform host protection does and does not do, and what sits in the gap between it and a real program
Registration and permitting status across the portfolio, which is a coverage question before it is a compliance question
Guest exposure, which looks like hospitality liability rather than tenancy and is often insured as neither
Off-season and vacancy provisions, the most commonly missed condition on seasonal property
Workers’ compensation for cleaning and turnover crews, including whether they are employees or independent contractors in fact
Three documents get most of the way there: your management agreements, your current declarations pages, and your vendor certificate log. If you have a claim history or a renewal quote in hand, send those too. If you have none of it organized, send what you have — assembling it is part of the work.
A written summary of where the program does not line up with what you have agreed to carry, ranked by what would actually hurt. Not a quote sheet. If the conclusion is that your current program is sound, that is what the summary will say, and there is no obligation attached to it.