Peter, everything you say here makes sense. The more think about it the more i believe my idea of a 30ft Trailer boat to explore all these areas.Leaving a boat unattended for months at a time is difficult. I remember one time my wife and I flew into San Francisco and got to the boat at 9PM. At least one rat had been aboard and made a total mess. We got a hotel for the night, and spent the weekend cleaning up and getting upholstery steam cleaned. Another time, someone had accidentally kicked-off my dock cord and the batteries were stone dead. I have a pretty long list of "and there was the time when....." stories from having been gone for a few months.
My boat was at Treasure Island Marina at the old US Naval Station Treasure Island halfway across the Bay Bridge. Although it's a great place to start a mini-cruise, it's a lousy place to visit on a vacation because there is not much there, and you need a car. For our last 6-months, we moved to Emeryville which had a shuttle bus to all sorts of places to eat, shop, drink, etc.
Now, I'm assuming you will not live on the boat full-time meaning you'll fly-in, perhaps for extended stays. But not all of your trips to the boat will involve heading out (I'm assuming you will continue to live in AZ) so even though little out-of-the-way towns along the Florida coast may have cheaper rates, if you're flying in, you'll burn up any savings on car rental and time, plus I'd get bored in these towns pretty quickly.
If I were in your shoes, I would probably look at something either in California or Sea of Cortez that you could conceivably drive to. San Carlos near Guaymus is a haul, but doable. You could dry-sail a boat (leave it on the hard while you're gone), and there's a decent ex-pat/cruiser community there. The cruising is pretty remote in the SoC, but should keep you happy for several years.
Winter cruising is better in Florida/Bahamas than SoC so if your heart is set on Florida, and if you do not plan to live near the boat full-time, I'd look to see if there are places you can dry-sail a larger boat. That would bring your costs way down, and would be easier on the boat. Possible some marinas may have a back-lot.
Good luck.
Peter
I think we'll either dig the trailer trawler idea, or find the sweet spot for a larger boat. I do have some questions about San Carlos. Is towing there a safe prospect?
Have you been there? Had a couple i met some time ago raved about it.