Another way to think about it is that I bet the worst deals ever done were modeled in a perfectly working model.

I bet nobody else does.

you should get a RMLO or an underwriter to qualify the borrower. if its owner occupied and in florida you also will need to use a third party servicing company to service the loan which will run you around $450/yr. not an accountant but its my understnding unfortunately the interest income is going to be taxed at ordinary income and the principal will reduce the principal. how you offset the losses talk to your CPA.your best bet honestly is to just sell it and bite the bullet. 

I’m Lauren, a professional with a background in web development, IT, and teaching computer science.

Some will pay to stay waterfront but there are just as many I’m betting that would opt for slightly less expensive digs in a very popular tourist destination. 

This is so important.4- Some platforms let you build pages, some let you build landing pages which are really just web pages that are designed for specific keyword phrases and sometimes don't include navigation menus to keep your leads from clicking to another page on your website.

I don't think the sheriff will do anything without an eviction having been processed which it doesn't sound like is necessary here.As for the cameras, I think Ring is probably your best bet.

Not to get off topic here but I find many members of the BP community spend more money and time creating complexed webs of entities than my former employer who owned over a billion dollars worth of real estate.

@Will Boller, in a quick click around on Interval International's website (https://www.intervalworld.com/web/my/home) a major exchange for timeshare properties, it seems like it is 50/50 from my small sample looking at properties in the northeast USA, with a handful allowing Sunday weekly check-ins too.Granted, this exchange is not an Airbnb, but it is all weekly stays in condos run, presumably, by large professional operators that have studied this business to maximize revenue.  

That may be your best bet if cash flow is your move.Florida will be great for appreciation, we still have people moving here like crazy.