Okay, I'm going to editorialize on the Orlando area.
The weather is pretty and there's LOTS to do, but by some standards Orlando has two big issues.
1. Crime is pretty high. Not as bad as NYC but still in the top 10% of metro areas for highest crime per capita.
2. Public school support for the Orlando area is below average. Funding is usually tight for schools and the number of pupils per classroom teacher is above average. Not that it's BAD-BAD, it's just not very good.
One other issue that may or may not affect you: lack of seasons. I know many former "Yankees" who are split on this issue. Some love the Florida weather and total lack of seasons (even around Halloween, Thanksgiving and Christmas) while others rue the day they moved here because of those very same reasons. Remember, you'll never have another multicolor autumn, cozy Thanksgiving or White Christmas.
Hey shoediva! I actually lived an hour west of Orlando for most of my life! I moved from NY when I was 8 or 9, and only moved from Florida when I got married in January 2003. Now I live in Houston, Texas.
What would you like to know about the area? My family still lives there, and I am very familiar with the Central Florida/Orlando area.