Pretty sure i've posted this before, so im sure you can find it if you look, but I am doing the board bum thing this winter. I had friends that wintered in VT and am sharing a house with them, and kind of got a hand getting a job (but it wasn't necessary, just easier). I'm pretty lucky cause I'm making decent money, but then again I have experience, and real responsibilities.
Advice: Go where the money is, look where I am. Don't go to some crappy little hill where you'll be getting min wage and so will your boss..head west if needed. get in town early in the season and talk to HR or whoever at the mountain. Ask about job fairs, what jobs are available, and what type of resources they have as far as housing, employee newsletters, etc. I'm thinking about going west next winter, still on the fence, either way I'll be having a great time...One thing I would change is I would get a job that starts in early afternoon and goes til 10 or 11 (im in foodservice), as right now I am working all day long, and miss out on some prime riding time (I still get out at least 4 times a week though, two of which are full days.
Go for it, I do have ambitions in life and have some dreams, but frankly, I'm happy, and will keep doing it as long as I am happy.