I have been having the same exact thoughts. Sleev-les and I were discussing it in the Local thread. I'm fairly new to snowboarding. Last year was my first season. I live in MD close to DC, so I'm about a 1.5 hr drive from Liberty and my folks also have a TimeShare at Massenutten. What I did was sign up at meetup.com and joined 3 snowboarding groups with people in the DMV area. So for this season that should allow for plenty of carpooling and bus trips to the local mountains as well as Vermont. So I did the math in how many trips it would take for the season pass to pay itself off, how many days I would be able to go throughout out the season (work and weather permitting) and how many of those days would I be going to other diffrent resorts. I just decided to get the Advantage Card it gives me about 40% off lift tickets at Liberty, Whitetail, and Roundtop and every 6th visit is free. All for $84.00 which will pay itself off easy.
I did one bus trip and it was the last time I'd ever do that. We took one to Snowshoe last year for a day trip. Not only is it a miserable ride, you get no boarding time. Next time I'll drive myself and stay for the weekend.