Interesting discussion. Mike, you seem headed for SE Florida, in which case offering you info on other
parts of the state may be a waste of (y)our time. OTOH one of the unique things about FL - and one of the things it has in common with
California - is its size & length, and therefore its regional diversity, culturally and physically. As someone who did what you are considering, I think you'd be best served if you stepped back for a moment and considered all of your key criteria and then looked at how the various regions of FL met those criteria. You may well find, as we did, that you'll end up being attracted to several regions to which you initially gave little attention.
In a nutshell (and so of course it's going to be grossly incomplete), here's how I view Florida when looking thru my lens:
-- Panhandle: more 'southern' than any other part of FL; limited population densities but also (relatively) limited resources & attractions; easier location from which to travel back to the midwest; the most 'seasonal' climate of any FL region; historically one of the areas with the biggest
hurricane 'bullseye'
-- NE area &
Jacksonville: one of the largest metropolitan areas (2.4M in its MSA) with the mix of
events, colleges, etc. that come with that; also seasonal climate but less severe in summer and
winter than the Panhandle; a unique/appealing
boating area (St. John's River) that's relatively uncrowded; relatively stable economy because of the large
Navy presence; the least likely area in coastal FL to experience
hurricane force winds (indented coastline and a distancing Gulf Stream)
-- Tampa Bay area: I'd maintain St. Pete has the 'best' (in features, resources and eye-appeal) waterfront venue in the state; another major metropolitan area (tho' without the cheek-to-jowl appearance and reality of the Ft. L/Miami area) with universities, sports
events etc.; daysailing easily done over a relatively wide area when you consider the large Bay and its barrier islands; another bulls-eye region but the one that will see the most damage from a 'hit' because it hasn't seen a Cat 1 or higher storm within 100km of the Bay's centerpoint in over 60 years...and its during that time that most of the land fill and construction was completed
-- SW FL: perhaps its most appealing feature is Charlotte Bay (Harbor), the only large estuary that the state has protected from development in perpetuity; like the Panhandle, less population density and also less in events, community resources and the like
-- the Space Coast: a long & protected Indian River is another major
boating resource for daysailing; one strip mall city after the next and without the metropolitan features and benefits as well as less aesthetic appeal; adjacent to the Abacos
-- I'll skip summarizing SE FL as you seem to already know much about that area
Two final thoughts: Assuming you want seasonal access to the
Bahamas, I think the only area that might be a bit of a liability in that regard is the Panhandle. I think you'd be letting minor differences make major decisions if you chose a region based on its proximity to the islands for the simple reason they are relatively accessible from most of FL. We recently sailed from St. Pete to the middle Keys in a
single overnight, from which it was a daysail (with the Gulf Stream) to reach Gun Cay and entrance onto the Banks and points east. Similarly,
Jacksonville is a
single overnight to Port Canaveral, from which many sailors depart for the Abacos (tho' points further S certainly make for a quicker run). If you had a 30' 400 hp powerboat and wanted weekend access, it would be a different story.
Also, give a second look at just what you plan to do during those hot/humid Florida summers. Hopping over to the islands will put you in an area with few hurricane holes during the cyclonic storm season and when its hottest and with the least
wind. Some find this the ideal time because of fewer
boats...but it is a trade-off to say the least. OTOH if you think you'll
head N on your boat to escape the heat & humidity, you'll find it consistently present all the way up thru the Chesapeake. My point is to consider that a move to the SE
USA is a move to hot/humid summers, no matter how you shave it.
Good luck on the
research. We think there are multiple very appealing choices here, despite Florida's many problems, but the devil's in the (i.e. your) details.
Jack