Ok I know this is irritating but here is some more information to chew on when giving us advice:
The above ideas make a few assumptions; the main one being that the boat will be in southern Florida.
The facts are however that the boat currently is in Newport. We are going to cruise July and August from there, probably spending time in NY and DC (visiting friends and family) and then some time in the Chesapeake. We then need to return home but plan to join the boat in December. My plan is to get a delivery skipper to take her South after the Hurricane season. Since it is then cold again however (and no heater installed yet), we're not relishing doing the ICW ourselves so therefore the idea of the delivery - and picking her up in Florida again.
We will then have six months starting December and want to make the most of it, given what I've said above.