I've lived in Orlando for the last 12 years or so. Personally I liked it a lot when I first moved here but lately I have been a bit homesick (VA). This is most likely due to my having a lot more close friends in VA. The culture is a bit of a mixture from what I see as almost everyone you meet is from somewhere other than Florida. Although, that may be from my living in touristville.
I'm not a cold weather person so having a warmer climate longer throughout the year is great to me but some people find the summer heat to be a huge pain. Plus the year round yard maintenance is a bit of a homeowner hassle.
As for the housing market, there are a ton of cheap houses from all of the foreclosures. A lot of bank owned houses are up for rent from not being sold very quickly so you could easily rent a house when you first get here before being locked into a sale. I will note that most major insurance companies won't touch houses in Florida unless you already have a policy with them so you typically end up with some small time insurance place.