I buy a season pass to somewhere (in this case Blue Mountain PA) I go very frequently and use it as much as possible, which is usually every weekend. I'll go to other places depending on conditions, crowded holidays, etc. but Blue Mountain is my favorite hands down. I probably won't consider anyplace else for me at least. Everyone is different. If you can, go to mountains that you'll consider buying a pass for and pick the best - Best conditions, location, lack of crowds, night skiing, etc. If you have a season pass for you favorite mountain, you'll use that pass often.
If I'm able to make a trip somewhere special like Stratton or Okemo or Stowe or Jay Peak (None of that has happened yet)... you get the idea, I will absolutely go for it. If your worried about price, you generally pay off the season pass after 8-10 trips. That's 3 weekends for me, and you'll have plenty of opportunities to go the rest of the season.
You're in NJ right? I am and many mountains nearby have a spring pass that is 1) cheaper than a regular pass and 2) valid for the rest of this season and ALL of next season. Blue Mt, Camelback, and Mountain Creek are all doing this. There may be others, but those 3 are the first that come to my mind.