Option 1: A summer pass last year was $950, you could save and get one, hitch to ski and live in a tent in the woods. A lot of people do this.
Option 2: Get a job at T-line, Ski bowl, or the Golf Course at the bottom of the hill. T-line gives you a pass every day you work. The other two have pass days that you can sign up for so it is not as good, but you'll still get in a lot of days. Working at ski bowl seems real relaxed and less uptight than t-line. The job you want at t-line is night porter/handy. Days you work you have to be in at 4-maybe 4:30 PM and it's pretty chill because most of the managers go home. That's pretty much the only job where you might be able to ski every day. I worked in the dining room a couple summers and pretty much ended up skiing 3-4 days a week and saved up bank.
Honestly the hardest part of it all is figuring out where to live for cheapish. If you roll out in May, bam, you can find a house. If you shoot out at the middle of June it's waaaay harder so work on figuring that shit out before you go. You'll need roommates unless you want to spend rediulous dollars on housing.
Oh and poach the hot tubs at the luxury living at mt hood condos. They're nice, you'll feel like a boss. Be nice to the dude who works there and go with less than 4 heads and you won't even get kicked out usually if they catch you.
