We have a site through our PMS (Streamline/BizCor) that facilitates the bookings through a site. 

I have never used that site.

One thing you might think of doing is having and promoting your own website to avoid the exhorbitant fees charged by the third party sites such as Expedia, Booking.com and Air BnB.  

Check out this site - https://theluxurypergola.com/blogs/louvered-roof-info/hurric...They cover wind resistant pergolas in general but I would make sure whatever you get will be able to stand up to hurricanes that happen there from time to time.

At first, I looked at the various real estate crowdfunding sites.

From the calculators I've looked at, it seems like it makes more sense very-long-term to hold on, but I'd love other's thoughts/resources (I'm not passionate about passing on as-much-as-possible to my kids when I die).From a blog post on this site about when to sell, one of the factors was when things have appreciated more than the rents in the area- but I wasn't sure when it was 'enough.'

Close to a cool little town, close to an area attraction, etc....Also do a search here and see how to screen guests, in addition to what the hosting sites do.... like no last minute bookings, no short stays....

Is your income considered variable in nature depending on job sites and that you do not work a set amount of hours per week?

It is a great site, but can be a bit daunting especially as you go down the rabbit holes of all the different options.

Either way it would be a grey area, selling a house with a different amount of units/bedroom/bathroom seems extreme though. its an auction site, I have seen auction sites miss the fact there was additional lots in a sale.