You pay all the expenses and you have to furnish it completely and you have to communicate with guests and cleaners and handymen.  

Perhaps some recommendations on cleaners that specialize in STR's.  

You’re leaving money on the table if you try to do pricing on your ownFind a solid cleaner and handyman (this may take a couple tries) as they are the lifeblood of your business and will help you with any last-minute requests that you can’t do being far awayUse a Property Management System (PMS) tool like Guesty or OwnerRez to automate messages and run your business more efficientlyGood luck and DM me if you have any further questions!

Ive looked into enzyme cleaners, and other chemicals, but havent found anything suitable for floors. 

You have to file a claim if you needed to keep any of the deposit.Most of my bookings come via Homeaway and VRBO where I get the deposit and then release it after the cleaners check the house for damage.

A big problem you’ll have in the Poconos is that contractors & service professionals & cleaners & handymen have a habit of being SOOOO unreliable that there’s actually a term for it: the Pocono Promise.It means when someone tells you they’ll be there at a certain time to clean your house or fix something & you never hear from them again!

Does anyone have recommendations for cleaners/handypeople in Annapolis that go above and beyond and will also help manage (obviously at a premium).

In case of an action, a FL court can very well not acknowledge the LLC because of conflicts...this is not to say that it will happen, but we would take it from a much cleaner approach and having things stay within states as they should.The bottom line, I would definitely not have the FL property (or any rental property for that matter) under my personal name so putting the FL property in a FL LLC (that is properly formed and maintained) is how I would approach it.I hope that helps, let us know if you have further questions.This does not constitute legal advice, it is just my opinion of a hypothetical situation.

You should also get a cleaner in every few weeks to clean common areas.

I felt like it was cleaner and offered more simplicity.