seasonal work 25 years later

Once a waitress always a waitress!
I did seasonal work when I was young and I am at it again I went back on the road again eighteen months ago and spent a year in Jamaica and this past summer bartending in Bar Harbor, Maine and I am now in L.A. Even though I am near the water right in Marina Del Rey, I am not really feeling the vibe here, its been so cold and it is a concrete jungle. I long for island life.
I spent some winters in the US Virgins many years ago and have always wanted to return.
Life is a lot different now, and I am also a little bit older, so I have no ides what to expect
There was a time when I got in my orange VW bug, drove to Miami, caught a plane to St Croix with only 350 US dollars in my pocket and managed to spend the winter there. (I worked for a water sports company and lived in a falling down place called The Pink Palace.)
I guess things have changed!
I am wondering about seasonal work in 2007??- (for a young at heart ,waitress/bartender) or any job that would pay my living expenses.(I have all sorts of experience in all sorts of things ) I am also wondering if I would be able to find cheap housing in a place where I can get by without a car. My need are VERY simple -
I know that the way to start would be to get down there and see what is up. Hotels are looking awfully expensive so I could not do that for very long.

If anyone on this board can offer me suggestions, advice, pros and cons , I would really appreciate it -

What island, you may be wondering - my answer to that is I am open minded - I would love to hear what some folks who are there or who have been in recent years have to say

if things go well, I would like to stay year round, just give me an Island in the sun.....