So, for example, a 4-night stay for a group of 12?

Any advice on how to just dive in? 

The trials you face—long nights, tough negotiations, setbacks—will all be worth it for the wealth and freedom you can create.

@Chris Lin,Thank you very much for spending time with me on the phone last night. 

But that's just me, maybe your market can tolerate higher nightly rates.....I agree with Bruce.

And the owner is very responsive to questions or issues (emailed him at night and received a reply within a few hours).  

Maybe an investor is flipping a lot of properties and you could offer to pick up and deliver materials to his crews, clean the work sites every night, bring his crew lunch, or whatever.Find a way to make yourself useful to them, and they will reciprocate.

Most won't insure pools with diving boards or ones without a VGBA drain.2) Include the cost of a pool company to manage the pool in the rent. 

Southwest Florida is definitely an exciting (but competitive) market, so props to you for diving in!

Stay there one night and test it yourself.