Our laws require us to offer a rental first come first served (first completed application that qualifies must be offered the unit).

Wanted to still be close to family but maintain a cheaper lifestyle, still have strong appreciation, and much better tenant/landlord laws, taxes, etc. 

Lastly, there's very landlord friendly laws here!

More than 5 days late (or whatever your local laws consider late), give them notice. 

Maybe the AI can keep you from calling people on the no call list and violating the law?

Regulations & Compliance: What's the best way to research local STR laws and avoid potential regulatory issues?

I don't invest in FL, so I don't know local laws, but find a real estate attorney that does and have a conversation.

Your local laws are going to prevail.

As long as you are following the law and the lease, you shouldn't worry about lawsuits.

I will not comment as to the tax laws and underlying rules - that is a discussion you can have with your tax advisor who presumably you are paying to help you.What I will do is provide practical and business guidance on tracking time.Firstly, there are apps available that can assist with time tracking where you can specifically detail your time, who you met with, etc.