This is a possibility for me as well, although it would be sooner than 40 years LOL. I'll be 44 in a couple of weeks.
In a similar scenario, I moved from New Jersey to South Florida about 18 years ago. My main reason was because I loved the beach so much in NJ, and you only got 2 months of it at best. I moved for the beach and the weather (no snow, and I hate being cold.)
I love South Florida, and I fully appreciate the weather (even with the hurricanes) but - I pretty much stopped going to the beach after the first few years. I go when we have out of town guests. But I don't generally go because you always think "it will be there tomorrow."
Plus, when you are on vacation, you are on vacation. When you are not on vacation in a vacation area, it's different. When you do have out of town guests, you have to remind them sometimes they are on vacation but you are not, and you can't keep up with all they want to do LOL.
Now, don't get me wrong, while we don't go to the beach, we can still go out in the pool in our own backyard almost year-round. This is where I belong to live.
We have considered eventually retiring either to the Keys or to the Disney area. I could easily see myself working at WDW, especially for the perks. The thing is, Orlando itself is not cute. I know there are nice areas here and there, but I've spent extensive amounts of time there, and overall, not the nicest place to live. I would look outside the WDW area most likely, unless Celebration is affordable.
When you live somewhere touristy, you are less likely to put up with the barriers you know you have to deal with on vacation. For example: just the parking situation near the beach is enough to keep me in my backyard. If I were on vacation, it would be an expected inconvenience and expense. I live 10 minutes from the beach but it can take 20 minutes to park. So I could see living near WDW and thinking hmmm...go eat at Be Our Guest or our local restaurant? Well, if I have to go through the whole parking routine at WDW, it might be easier to just go more often to our local place. No wading through children and strollers, no (sigh) tourists - you'll be surprised how quickly you start talking about tourists that way LOL.