Cory, re the train-wreck feel to VMMCM: try fast-forwarding past any parts with human guest stars.
Seriously! I watched it again this past week (seen it about 3-4 times now) and the movie flows much better without most of them. I think more judicious editing and better human actors would have helped the movie considerably. I'm not fond of all the product placement, but as already noted, M@WDW showed it can be done entertainingly.
Aside from that, it's just a matter of seeing things slightly differently. Dark Crystal is a stunning technical achievement, but I never cared for the story or the characters. Don't Eat the Pictures bored me (and slightly creeped me out) even as a kid. So I wouldn't want new Henson stuff to resemble those. I will agree that there was at least an attempt at innovation in those projects that could be felt more strongly in the recent stuff.
Frogboy: Two words for the next holiday special: Bastille Day.
Seriously though, I think you nailed exactly the same parallel I was thinking: the Peanuts specials. First came Charlie Brown Christmas, then the Great Pumpkin special. This seems a natural progression for the Muppets too. And I agree with you that we sorely need an updated Valentine's Special. That doesn't mean every Muppet TV-movie ought to revolve around holidays, but it'd be a good launching point for some of them and would get some casual fans' attention: "Oh, the Muppets' take on Valentines' Day? THIS I gotta see." Eventually I'd like to see a Thanksgiving and Easter special as well (with puppet Muppet Babies on the latter, introducing Baby Pepe!), but not immediately after the others. They should switch gears somewhere in there.
I hope Henson's done with Christmas specials for a while. Christmas is my favorite holiday, but ENOUGH ALREADY. The studio's produced so many specials about this holiday with both the TMS cast, the SS cast, the FR cast, as well as numerous one-shot specials. I'm sure there's a Bear Christmas special that I just haven't heard of yet. And none of them is going to top MFC. Heck, just show that again on a major network every year! On TV, they'd be able to show those scenes that always get cut on the video. Aside from Piggy's hair, I can't think of anything really dated about the special. Muppet fans would be thrilled, and the casual fan would be none the wiser. I say they should go for it! (After VMMCM gets at least one more airing, of course.)
The next part shouldn't be read by anyone from JHC, for fear that they can't use the idea for legal reasons. This is just me hoping out loud to my fellow fan/friends:
If they do make a Halloween TV-movie, I hope Clueless Morgan is involved. I didn't care much for MTI; I only saw it once when it first came out. But I still think of Clueless Morgan in his two scenes and I laugh every time I do. I guess they used the character along with Polly the Crab in some lame UK skits where they were waiters or something, and then pretty much forgot about him. Clueless is funniest when he's scared and trying to come up with an inept solution to his problem, i.e. someone swings a sword at him and he says, "Oh, wait, okay. Ummm...I'm dead!" then obediently closes his eyes and falls over! I could see great potential for that kind of character in an allegedly haunted house. (Of course, in the end they'll find out it was Farmer Jenkins with his counterfeiting scheme, etc.)