previously, i never bought a pass because i enjoyed trying out new mountains and never skied at one mountain enough times to hit the break even point. also, due to discount hunting, i have yet to have a season in which day ticket prices have much exceeded the cost of a season pass.
now, having skied at pretty much every major mountain in new england except smuggs, stratton, and mount snow... i have a pretty good feel for what is out there. i don't feel the need to hit up as many new areas as i know they aren't as good as my favs just looking at the map and stats. also, living closer to the mountains, i know i can log many more days and be more willing to drive for suspect conditions or during iffy weather. essentially, the cost/benefit ratio has tipped in favor of a season pass. i still plan to get out to about a half dozen favorites and as much BC as possible, but i know that i can easily log 25-30 days alone on a season pass without even counting other areas.
it all comes down to cost/benefit in my book. will you get in enough days to break even and will you do so easily. if it is close, i would not opt for a pass. it would have to be significantly more, especially considering the pass locks you into one area, which is fine if you only want to ski one place, but i find that gets boring even if it is a great area.