I'm rereading Vineland atm and loving it. It's miles better than I remembered. The structure's insane; flashbacks inside flashbacks. He's on top form prose-wise too. I reread Bleeding Edge a couple of days ago and enjoyed it even more than last time, but going back to this one's really shown it up. It's longer, but you can tell he doesn't have the same command of his talents by that point. There aren't as many of those dense, descriptive paragraphs and he leans more heavily on gags and pop culture references.Actually just looked again... seems like Vineland is bottom according to everyone but me. But the rest stands. Consensus?
I haven't finished the reread yet, but I think I disagree with @Slothrop on Vineland's handling of the counterculture now. I'm up to the bit where we hear what happened to Weed Atman and, so far, my impression's less that Pynchon fully believes in the revolutionary potential of the 60s and more that he thinks there's something admirable in opposition to the state and that the response and behaviour of the American state in the 60s was so appalling he can't help sympathising with the counterculture.
He shows the hippies doing some brave things and having certain ideals at one time or another, but he also shows them screwing each other over, not really knowing what they're talking about and making stupid decisions. It's not a particularly rosy portrait, even if the police etc are the big bad.