We have room to do a nice home theater system with a sectional and video games and lose the pool table.  

Theater and art majors - run the other way!

How is the building set up, equal sides in an open space, long and narrow, widthXlength can limit options or themes, it may not be a great dance floor or live dinner theater setting, lounge, etc.ADA compliance, how accessable is the basement, does it have more than one exit, an elevator?

It seems that restaurants, gyms, movie theaters, hotels, etc. are going to have a hard time coming back.

We are turning the 2 car garage into a theater room, redid much of the flooring in the house, added a sauna, etc.

Perhaps nearby more country residents see Cleveland as their closest big city amenities for higher end options, museums, theater, concert, sports etc.    

And a lot of them are going to include things like arcade machines and theaters which will constantly have issues and are difficult to service.Do you have the proper licenses to manage other people's properties in Florida?

Turning the pool table loft area into a full-on game room, or maybe even doing a projector screen with a home theater or video gaming set-up there - that could be a huge selling point for families looking to book a stay with amenities and spaces that will help keep their kids occupied and entertained.One note on the existing hot tub: having an awesome, well-running, clean hot tub can definitely help you command a nice premium on your STR bookings. 

"My wife was going to a dance/theater school out there" I moved to kissimmee FL last month.

The attractions in Detroit (casinos, stadiums, Fox Theater, Bell Isle, etc) pull the middle class from the suburbs for a few hours, but they go back to suburbia afterwards because they will never live/raise a family near downtown.