While I do not live in the Keys myself I have a friend who lives down there. All though for him it was not really a pack up and go for broke thing. He made his money and lots of it and lives very nicely. His biggest worry in life is how will the waves tomorrow morning effect fishing?

must be nice.
Now me on the other hand. I can really relate to your post. While I am not in the Keys, and those were the original plan. I think I got pretty close and am very happy with my decisions.
I was working in a very good dream job. I was doing exactly what I wanted to do since I was a kid, went to school for, and became very successful at it, yadda yadda.
One night I just got sick of sitting around the poker table listening to everyone say " yep, one of these darn days, im'a gittin on up outta here". Been listening to people say that for a long time.
So I quit my career dream job, sold everything I owned, and bought the next Greyhound out of town. Two days later I ended up in Orlando with out a place to live or a job.
Five years later, I am very happy that I moved the way I did. The only regret I have is selling my stereo set up. It included some speakers my dad had passed on down to me. Those babys were made of oak and had some super sound. They just don't make them like that anymore.
Anyway. While going that first two weeks without a job and living out of a hotel was scary, it was well worth it. I could not be happier then I am now living in the sunshine state. I would not trade it for anything. I have a great job , a new career, with a great company. Of coarse with the training and experience Iv gained it will deffintly help if the Keys lure me down there on a permnent vacation.
I am sure there are plenty that will slam me for saying FLA is the best. Many complain about the heat ( the heat is why I moved down here ) the hurricanes ( small price to pay for living in paradise, Ill take a hurricane over a blizzard any day of the week )
Key West will come in time. I venture down as much as I can. It's only seven hours away. For now it is my one particuliar harbor. I'm pretty happy with that.
Point of all this is that if you want to do it there is nothing stopping you. If living in the Keys or anywhere in FLA is the lifestyle you really want, then it does not really matter what you do for work.
I'v met so many different types of people in my visits to the Keys. Alot of them are people like you and me. Folks who wanted a different lifestyle. Its all about 50/ 50 to. Half of them are working jobs like pizza , bouncer, bartender, bike rentle. They are so happy. It is exactly what they wanted. Yes they don't have the status they had back in " the world " But if it is the atmoshpere you are going for....who cares?
The other half did not find what they were looking for. Found out it is not exactly preserved the way it was in the 70's and after three months are ready to pick thier snow shovel back up.
I think if it is something you want, go make a few more visits. Spend a good two weeks there. Meet people. Make your own speculations.
Check your PM Im sending you a good job souce site. Good luck brother.