i have a few thoughts.
skiing (at a resort) costs money, therefore my first, gut reaction thought is that if you are obsessing over spending money on a season pass you probably shouldn't be skiing in the first place.
that said, there are plenty of options.
in Tahoe places like Heavenly have cheap passes that have blackout days (i.e. peak holidays).
other resorts have mid-week passes.
in Tahoe there is a deal called the Tahoe 6-Pack where you can purchase 6 tickets which are good at a variety of resorts. the cost comes out to be $46 each, which in many cases is about $15 - 30 off the regular daily ticket.
honestly, though, i buy a season pass and then i make sure that i ski its worth.
last season i bought a Colorado Pass.
i do not live in Colo.
i drove out and skied Colo twice and logged about 15-20 days on my Colo Pass, so it paid for itself.
i didn't buy passes in Tahoe, but rather shopped around for discount tickets, scored friends/family tix off ski buddies and the like.
again, i feel if you are obsessing over the cost of skiing then perhaps it's time for a cheaper sport (that said, all one has to do is shop around for cheap deals). Also, if you really want to get serious about it, the advice from a lot of folks about moving to a ski area is pretty sound.
i guess the best thing to do, if you are counting pennies, is to seriously estimate how many days this coming season you are going to ski. If it's only 5, then why buy a pass. If it's 40+, then a pass might be the ticket.
you need to figure out where you're gonna be skiing and how many days.
me, when i bought a pass it basically forced me to ski. i went from 40 days to 62 this past season because i bought a pass and i wanted to make sure it didn't go to waste.
but then i'm a weird nut. honestly when i go skiing i don't like to think about all the money i'm spending. i just go and have a good time and scrimp where i can (bringing my own lunch to the hill, sleeping in the truck or in hostels, swapping my decent cooking skills for the use of a couch, etc).
where there's a will, there's a way.
oh yeah, the other thing about a season pass is that it locks you down to one resort (unless you get a multi-resort pass, of which there are very few). Personally I enjoy mixing up my skiing and hitting a variety of resorts throughout the season (I try to ski at least 1 new resort a season).
i've always hesitated buying a pass in Tahoe that would lock me into one resort as some days I feel like riding Sugarbowl and others I feel like going to Alpine and one always has to make a ceremonial trip to Squaw.
so, to recap, if you want to be locked into one resort, buy a pass. if you plan on skiing at least 40 days, buy a pass (though do the math to see how many days you'd have to ski to pay off the pass as the days may vary). otherwise just roll with the daily tickets and enjoy the variety.