I think there aren't as many places to ski around Portland, so the ones that do exist are packed, I've read consistently that most of the time, you're waiting to take the lift, waiting to do your run, and then back to waiting for the lift. But if you don't have a 9-5 you can get out there when others are working and its great.

Also, $100 for a day of entertainment is a splurge. I have a decent income and probably only spend that much on a day-activity once every quarter or 2.