We're considering relocating to Florida in the next 2 years or so. Trying to get a feel for the area so we have a "plan" in action. We will definitely fly down at some point to see the area in person, but would like to get a "feel" for the different areas from locals. We are familiar with Orlando and southern FL but not with NE Florida.
Tired of the cold/long/crappy winters in Chicago.

Have lived here all our lives but ready for a change. We live in the northern 'burbs of Chicago and like the area but we've "seen it all" as they say. We need some new surrounding. The housing prices are out of control

and we're just tired of the area. My husband works in schools and does consulting so he can basically work anywhere. Our parents are getting older, their health isn't so great

- heck, I've had my share of health problems myself lately, so being somewhere with milder weather (warmer) would definitely be nice.
I read one of the city-data forums where someone jokingly mentioned there are different areas of Florida (Chicago-FL, New York-FL, Havana-FL, etc). I'm sure there is some truth to that, though! It just depends what you are looking for, I guess?
We live in a town of about 25,000 now. All of the towns are very close together, one after the other, so it's not liking you're driving from farm town to farm town with miles of land in between. We like that - because there is a lot to do, and you don't feel so isolated.
What areas of Florida are like that? With decent shopping, culture, restaurants, schools and business. Is it too much to ask to have an Ann Taylor Loft or a PF Changs (ha ha) around the corner, as well as the local restaurants and shoppes? Low on crime, with parks for biking etc? Something with a mainstreet or "downtown" where they have a farmer's market and you can meet up with friends?
I realize there is no utopia, no matter where you go - but to find a town in Florida that offers as close to those offerings as we can get and we'll be happy.
Now, weather -- we're thinking somewhere in central-Northern Florida. I'm liking the St Augustine area so far, but not "seeing" it myself, it's hard to get a feel for the area. Is it all highway driving to get anywhere and is Jacksonville as crime-ridden as people say?
Our different family members are all in different price ranges, when it comes to home buying, so an area with all offerings would be great. My parents would probably end up in a 55+ community which I think they would love.
How is the weather in the winter/summer near St Aug? I don't mind 50-60 degrees in the winter. It's the subzero temps, snow-blowing and ice we're trying to get away from.

I hear hurricanes are less likely up in that area (direct-hit) but in Florida you are always taking a chance.
Need somewhere with good healthcare (hospitals/doctors), some holistic/alternative health offerings nearby. I realize the mayo clinic is in Jacksonville which is a huge plus.
If my sister and her family joined us (her husband works in healthcare field - sales/marketing) what is available in terms of jobs/industry in the area?
If there are other areas/towns in FL that more or less fit the bill, please let me know. Too much to ask - yes, I'm sure. But any info or advice you can offer would be very much appreciated. Thanks!! I can feel the FL sunshine already.
