I've done ski leases in Kirkwood for the past three seasons. We rent a place in base camp amongst 10 people. It's a sweet setup. The lifts are across the street, you just come back in for lunch or if you want to switch to a different pair of skis. The best days are the road closure days. I've had a few days when it dumped and both roads were closed. Only people staying at the resort were able to ski for the first few hours -- makes the freshies last a good bit longer.
Overall, the lease runs about $1,200 per person for the entire season. Not exactly cheap, but can't beat the location. We also charge guest fees to offset the costs.
As for the 6Wood passes, a few of my buddies have done those in the past, but reliably they've wanted to ski some of the blackout dates, since everybody else was skiing, and it was good. So they ended up spending the same or even more than you'd pay for the discounted full season passes.
I prefer the drive up 88 compared to 50 any day (the number of clueless idiots on the road seems to be much lower). The only big downside to Kirkwood is night life. The only two bars in town (Bubbs and The Towers fka The Moon fka The Battered Beaver) get pretty desparate after about 9:30... The Moon sometimes has a local band, not too exciting. If you're staying in a place that is a member in the KCA (Kirkwood home owners association), you may have access to the KCA lounge, which has wine tasting every Saturday night. Other than that, the only night life is a bottle of wine in the hot tub...
Anyways, hope this helps.