We are considering a move to Florida and are going to look at Sun City Center near Tampa in the next few months. We have friends in the area and it seems warm enough to us. We don't plan to move until 2011 to wait until I am 59.5 years old and to wait for the Florida real estate market to calm down.
From looking at homes on the Internet (ziprealty), we think we would be interested in one of the 1960's homes in SCC.
In the area that you mentioned, do you know of any 55+ communities that have older homes like SCC?
We would like to minimize our home insurance and property tax costs -- and it seems that a great way to do that is to purchase an older home. The older homes in SCC can be puchased for 80-120k.
I can't speak to that myself, but there are definitely deals to be had in that price range. If you post the question on City Data forum for Fort Myers/Cape Coral, I am sure you would get many opinions.
For single family in older neighbourhood, I would agree that it is important to move where you already know someone....generally, one needs to think about social appetites and social strategy, or you are going to start feeling edgy from being isolated.
For insurance you have to consider being away from the coast and inland rivers/sloughs. You need to learn about FEMA risk ratings and make sure you are not in a high risk area. For older homes, you need to think about the status of hurricane upgrades to get discounts...post 2000 (can't remember exact year) homes were built to higher hurricane standards in Florida. Talk to an insurance rep BEFORE buying a property...better yet, educate yourself as a renter first...simply by talking to neighbours and hearing about all the mistakes they have made.
Indeed, in this particular environment, monthly upkeep is more important than price. Home Ownership Associations (HOA) fees, Taxes, Community Development District (CDD) fees, Insurances (Plus flood), Cable, Home Minding (required by insurance if not gated), AC electric, phoneline all adds up. Not being in an HOA area saves money, but then you have to make sure lawns are cut etc and then there is the problem of neighbours not doing upkeep and leaving junk in thier yards.
You also have to manage the risk of bankrupt and mismanaged cities, counties, builders, HOAs, neighbours, affiliated golf clubs and so on. The best way to enjoy Florida, with none of the risks, is to settle in as a long term renter, that way you can pack your bags and move to the next better area when trouble starts, and all your owner neighbours will be crying. This is a conclusion I came to when analysing a retirement move to Panama a few years back, that did not get executed.
It is hard however to give up the pride and control of ownership, and to have your neighours look down on you as a "mere" renter, then there are the risks and tax consequences of where you will put your house money capital and income if it is not sitting in your residence.
The sweet spot is to start out as a renter, and at some point, once all the skeletons are out of the closet, and you are fully aware of the various crises at the city, county, builder?, HOA? level, you see a deal that you cannot pass up at end of season or summer, and make a clever insider move, rather than an impulsive yankee sucker move.
But then you are the one looking into it. As long as you are aware of this issue, I guess doing the research is up to you (I have my hands full investigating tornados and sinkholes in southwest Missouri). 
