Even if you do preventative things it won't keep it dry.

True, However if you evict and you don't have it, they'll give you a short time to get the clearance, then they'll put an injunction on you, Legally preventing you from re-renting the property.

I tried doing that with my personal credit card but am having errors preventing me from doing so.

Since it is going to be a rental, first concentrate on any items that need maintenance immediately that prevent it from being rented now (creating cash flow)(including all parts to be working, such as HVAC, plumbing, electrical, etc.). 

As far as navigating STR laws/HOAs, I think its best to have a PM with experience operating STR's specifically in KC to prevent as many headaches as possible and answer any questions you may have before-hand.

It prevents me from transferring money to my crypto exchanges and I end up wiring money, which gets expensive.

By having shorter tenancies, you can do more preventative maintenance to take care of your property and make updates between tenants that allows you to increase rent even more. 

Buying a new build could be a good idea as well to prevent maintenance costs, but if you’re trying to BRrrr than bad idea.

Staff cannot ask about the person’s disability, require medical documentation, require a special identification card or training documentation for the dog, or ask that the dog demonstrate its ability to perform the work or task.I can't speak to Florida law but Federal regs are in force.In the end, you just eat the extra cleaning, if any, but you can charge for damage caused by the guests or service animals.So in both cases of our service animal guests, they were excellent with zero issues.EDIT - The stupid forum prevents me from putting a link to the ADA rules -https://www.ada.gov/resources/service-animals-2010-requirements

They’ll also keep abreast of the laws and prevent violations.