As for relocation, the big question is whether you want a 55+ community or not. They have their advantages and disadvantages, so it's good to think about that before you even begin to look. If you decide on one of those, there are all kinds, ranging from entire cities (the Villages or Top of the World) to small developments. If not, then it's all a matter of what kind of community you choose to live in, We started in a 55+ and this year moved to a regular neighborhood, where we are much happier.
BY the way, Orlando is a wonderful place to visit and has some very nice surrounding communities, but you need to consider the disadvantages, chief among them the truly oppressive traffic. If you have to go anywhere involving a major road, you will experience traffic. It's okay when you are visiting, but to go through it on a daily basis is not fun. We visit Orlando a lot to use its airport and to go to the parks, but I would not live there on a bet.
I wanted to live in a coastal community, and we picked Vero Beach because it's the northernmost point where you can comfortably get in the ocean 12 months of the year. It seems like a little thing, but when you're moving to Florida to be able to go to the beach, you want to be able to do it at any time of year, it seems to me. So now we live about 5 miles from a beach and have access to maybe 20 more. We're not so close to the water that hurricanes or flooding should be a problem. And I feel a lot more connected to the town than I ever did in a 55+ community, where, in our experience, you get connected to that development and not much outside it.