Orlando is an interesting place. But, as noted, it is in Florida, and the state government as a whole is not very trans friendly. The 'hip' factor to a large degree centers on the rave culture and there is a lot of electroncia/techno music that is HQed there. But, if the rave deal (dropping X and dancing all night) is not your thing, the hipness factor slides off fast. The gay scene - as noted in South Beach and Key West - exists, thrives even, but those areas are very expensive.
The industry in Orlando is tourism, and to that degree there are two kinds of service jobs. Ones with public contact where they seem to prefer bright, shinny, young 'Disney Youth' types, and hotel maids, cooks, janitorial, dishwashers who are all pretty much speaking Spanish. And the speaking Spanish deal goes for lots of the tourists too, as Orlando is the number one vacation destination for South America. So if you speak fluent Spanish that would help. And, as noted, those jobs do not pay a whole lot to begin with.
You can stay with someone else, but for how long? A week, a month, a year? At what point - if you don't have a job - does it get oppressive for her to have someone sitting around the house who is not contributing? My guess is, not very long at all.
I'm also sure that the recent oil spill, as such things do, had a spillover effect on Orlando tourism, so that industry might not be hiring as much as it did a year ago, and it might take some time to rebound, as tourism on the whole, nationwide, is not doing as well as it did five to ten years ago. And if they are stating that the unemployment rate is 11%, the real number is much, much higher, perhaps as much as double that owing to how such numbers are calculated. And outside of tourism there is very little else, no heavy industry or manufacturing, no major higher educational facility, no large clerical based stuff like banking or insurance.
