I also see you have a 7 night minimum athe the 2 bed in Sarasota.

I own two rentals in Indiana.

There isn't enough information in here about the current state of the house to be able to advise you, but I would think #3 is a definite no as it seems unnecessary from a cost perspective although that market has scale to accept it.

Then you can read a more in-depth book like The Book On Rental Property Investing by Brandon Turner or The Unofficial Guide to Real Estate Investing by Spencer Strauss.Here's a guide that teaches you how to analyze a property.https://www.biggerpockets.com/blog/rental-property-cash-flow...Finding deal that cash flow is the easy part.

Figuring out the true cost will heavily depend on the type of dig down, depth, and total square footage. 

Then you can read a more in-depth book like The Book On Rental Property Investing by Brandon Turner or The Unofficial Guide to Real Estate Investing by Spencer Strauss.2.

On the other hand, tenants tend to cause damages when moving these appliances in/out, so having them in place may be safer.I recommend you look at what others are doing in your community and price point.

@Bryan Zayac  In PA, there is a state document called the Municipal Planning Code MPC. 

For instance, in places like Austin or Chicago, I’ve noticed similar deals pay off when you have the right property management systems dialed in.

When I was in college, my landlord would just walk into the house uninvited without even knocking.