Intersting thread. Let's see, I grew up in Pittsburgh (Aliquippa), and lived in Orldando for four years in the mid 90's (Windemere), so I have opinions about both sides....
1. Orlando was fun to live in. Being AP members to WDW, Uni, and Sea World was a blast. Also, if you are a golfer, it is heaven.
2. Orlando home prices are very reasonable compared to most markets. You do need to be careful about the builder though, but if you get a good one (I had the best, Rick Carr of Sunscape Homes) you could have the house of your dreams for not much money.
3. The environment is VERY different than Pittsburgh. Pittsburgh's ethnic mix and pride, the small towns that banded together, etc, are unique. Folks are friendly in Orlando, but it's not like living in a smallhamlet outside of Pittsburgh.
4. The no winter thing is appealing, but I started to miss it. Then again, I've lived in Philly for the last ten years and I hate snow again !!! The heat in Orlando in the summer is extreme, but you learn to live with it.
5. Don't ever expect a lawn like up north. What goe for gras sin Florida, would be pulled as weeds in the north
. Oh, yea, don't step on a fire ant hill.
6. Lots of high tech business in Orlando. Much more than most expect. Much of it built around the military-industrial complex, but good jobs and good money.
My wife and I will be retiring in ~ 9 years. What our boys do (either stay close by up here, or scatter across the country) will determine where we retire. If it is not here in PA, it will either be in Florida or in Albuquerque..