The unavoidable facts of life in Florida. There are severe hurricanes. We have been thru three cat 3 in our 30 years here. Some areas are worse than others for damage.
Thus, insurance for flood or wind damage is expensive, and in some cases difficult to obtain. I have been able to retain my original USAA insurance and they have treated me well--with claims after each storm. But I have paid high premiums.
There is no state income or personal property (boat) tax. Because of this, the property taxes have a high millage. The sales tax is fair.
We found the living in Florida was a very significant savings from living in S. Calif. 30 years ago. Car and RV insurance was less--boat insurance, as long as you had a way to get the boat out of danger (haul out onto hard, trailer out of area, or secure in a protected basin like behind our home. )
Initially waterfront property was relatively in-expensive. It has gone way up this last year, and I don't think it is sustainable at that level. Homes in our subdivision (about 40 homes, secluded peninsula, with water on both sides--bay and bayou.) Have gone for as low as $240,000 (house which has bad damage after each hurricane, and sold for $100,000 less than it sold for 3 years ago, to one which sold for $890,000--also flooded, wind and wave damage after Sally for a 2400 sq foot home on a single lot on the bay.
There are some awesome critters who have been here a lot longer than us white men and women. Alligators, panthers, bears, coyote, bob cats, poisonous snakes: water moccasin (most common), eastern Diamond back rattle snake, copperhead, coral snake. (We have seen all of these critters in the wild during the last 5 years in our travels). Mosquitoes the size of F16's, don't exist--and we don't have much of a problem in our area since we have excellent populations of dragon flies, who just gobble the mosquitoes up. However we do have part of the back yard and the pool under a screen enclosure--and it makes living a lot more comfortable.
As for where to live--Keys are regularly devastated by hurricanes. During season, there are many tourists. We spent 7 winters at a waterfront RV park, with a boat slip. Unfortunately that was turned into condos. The weather was good--with occasional northerly winds. The tourists were not a problem since we avoided their haunts. We subscribed to a concert series, and thus got to know a number of full time residents. This enriched the whole experience. The folks in the RV park came back every year--many from Canada or the Frozen North, Like Wisconsin.
I would not want to live there full time. The summers get much hotter, and at least on the weekends some less than what we considered desirables from Miami and Hollywood descended on the Keys.
We chose Pensacola because of the good airport, good health care (3 major medical centers), 3 universities, excellent arts and music venues almost every week. The life is less laid back than 30 years ago when we first bought a property here, but in comparison to other parts of Florida--this remains the "Redneck Riveria". Incidentally Mark, you would love the political attitude here! Law enforcement is well respected, and we. have excellent Sheriff and Police Departments.
There are many other areas along the coast from Penscaola--where we are at the most Western part of Florida, to Fort Walton Beach, Destin, Panama City to the more 'rural areas like Franklin Co. and Apalachicola or Carabell and the (expensive now) "forgotten coast".
We used to travel to Fort Lauderdale, when on the BOD of SSCA--I loved the people I was associated with--I hated the Miami and Fort Lauderdale crowds. Worse than LA or Seattle at rush hour! We also spent some time in Sarasota--and that was very crowded during the high tourist season.
The waterfront real estate in S. Florida has become rather expensive. We had looked at Cape Coral 30 years ago, and the houses were in the $30K to 70K range--a number of vacant lots still. Now those homes are close to a million dollars.
I might be looking at the Burnt Store area. Venice and that area waterfront is expensive.
If you don't want waterfront, I believe that there are going to be a number of nice homes in central Fl. Stay away from the large cities like St. Pete, Orlando,
I agree with Colby that the St. John's River is a very special place. We could see ourselves living there. But it has a climate not too dissimilar from Pensacola, where we have "winter"--with the occasional frost and even snow once in 30 years. There can be flooding along the river. We (and I expect Colby) have experienced it mostly in March. March thru April is prime time. Even in those times the river and good anchorages can be impacted with weekend boaters.
A quick perusal of the real estate for sale along the St. John's is going to be expensive for a really new and nice home. However there are some very affordable lots and other houses, a bit older--maybe concrete block, or 50's construction that look to be decent. Off water, there is a huge variety of homes--as there is all thru "old cracker Florida".
On your next journey to Florida, visit "Camp Thataway". Full hookups for RV, Dock with water and power, always a free bedroom, except perhaps at Christmas time.
. The boating looks great, the weather, fantastic etc. Lots of people but there are lots of people here too and it’s not nearly as attractive. 
