I'm coming from the steveturner/mdf perspective.
Overall: for me it's still mostly about terrain. Not necessarily all double blacks, but "interesting" with character, scenery, variety, and especially low crowds. I like an empty day at a megaresort, but also can greatly enjoy mid to smallish places under the right circumstances. I enjoy discovering places that are new to me and/or off the beaten path for many folks. I prefer skiing weekdays or other non-prime times, but do weekends too.
Value: I generally tend towards budget ski experiences and often stay a few miles from ski areas on overnight trips, but will pay for luxury accommodations and state of the art infrastructure if nicely reduced due to low season or other discounts.
Grooming: got to admit I like high angle grooming. An all day dose of bumps is too much for me now. I like areas with a lot of undulation too, as opposed to a strictly straight-down-the-fall-line layout. Gives old bones a rest between intensity bursts. I like more open glades, can't handle super steep and tight. Hi speed lifts are nice, but not mandatory for me.
Après ski: my idea of hot nightlife is a hot tub and a cold beer. Haven't been to a disco since they called them discos. But easy skiing wife likes dining out, shopping, and sightseeing and I'll tag along for some of that.
Misc: I too have a teenage son for an advanced terrain ski buddy, in fact he as surpassed me in the bumps and glades categories. Last big family ski trip he and I skied 5 days straight, while wife and daughter skied only every other day. They shopped and did sightseeing around Quebec City on off days.
Boomers with empty nests (mine still half full) should have more flexibility with vacation timing. I think resorts should really go after them by offering very aggressive "senior deals" in late season. Get them to buy into a cheap ski and stay, and then they will spend on dining, shopping, sightseeing, etc. Should also add that value driven Boomers don't need mega resorts. Some of the best recent experiences I've had were pulling into quiet parking lots that were just steps from the lifts at places like Eldora, Loveland, Le Massif, Plattekill. I still occasionally do "guys only" trips, depending on the mix of people those can be pretty hardcore, with el cheapo motels, bag lunches and pizza for dinner.
BTW Pete, which do you like better Silver or Schweitzer?