Catering can be lucrative. Work two events a month and boom, you've got rent.
Seasonal labor is great too, but don't expect to make a lot of money right off the bat. Learn now while your young and living at home so that come college/ski bum time, your making more than 10 bucks an hour at your first roofing job.
Find some sort of freelancing job that either A) facilitates travel or B) allows you to telecommute.
get into judging park,pipe, and moguls. the governing bodies will pay your travel expenses, hook you up with lift-tickets day of (an usually a day or two after if you can sweet-talk the events manager), and a place to stay. Bring your own food so that your per-diem can be turned into fun-time money.
It all comes down to prioritizing. If you want to ski around 100 days a year and travel to some cool places, don't expect to live in a sick house, go out boozing with your buddies every week, and have basically any hobby outside of skiing.
Oh and expect to be dead broke in May. it'll happen. But it's pretty goddamn rewarding to look back on a season and realize you didn't really have a job past the end of december, saw some amazing new places, met some kickass people, and skied your heart out.