Also, James Dainard just came out with a new flipping book, The House Flipping Framework.

The tourism authority has had some good information in the past about how many visitors come to each island and, of those visitors, how many book STRs.

What I love about Baselane is that it was built BY real estate investors FOR real estate investors so it's really dialed in to what you're going to need in order to prepare your taxes, keep your books up to date and the more operational aspects of being an REI like tenant vetting and processing rent payments.

I would recommend to read a few books.

I've obsessively been listening to every podcast episode I can, reading all the books, and signing up for any and every workshop and educational seminar.

Some say it increases bookings, while others mention concerns about damage and additional cleaning costs.

Finally, what’s the rate of return for alternative investments? 

Brandon Turner's Rental Property Investing book is an excellent primer to understanding the happy path for purchasing a property - however in this market it really comes down to having bulletproof assumptions on rents/taxes/R&M/etc. as with rates as high as they are/inventory as low as it is, there is less cushion in your returns if you analyze properties with bad assumptions.

From personal experience, this can motivate them to do a final deep clean before handing over the keys.Finally, for peace of mind, you might consider consulting a local real estate attorney.

2) How booked out are they?