I lived on the Rock for a brief while about six years ago. I had a very good job as far as jobs go in KW. I could actually afford my tiny, waaaaay overpriced s**thole studio in Old Town. Nonetheless, it took a about a month to figure out that FOR ME the idea of living in Key West and actually living in Key West are two very different things. It took a little longer to get out.
I think I would have loved the KW of 1958, 68, or 78- but then again that could be the romanticism talking that brought me there in the first place. I do know the Key West of 2008 is not for me- see Thal's post.
Today I spend a ton of time in the Keys working- usually every other weekend. I see no need to ever venture south of Big Pine Key. I plan on moving to the Keys in the next few years as I love it there, but KW wont be an option. It is sad what has happened to KW in the last few years as it is such a beautiful place as far as history, houses, and the true conchs.