I have to agree with statements made that New Vegas isn't the best game to watch. There's too many choices and it can be frustrating to watch a player pick a path you don't want, I don't think there's that much to be made fun of (hence why I call Toby's playthrough interesting. He actually manages to do things out of order enough that weird stuff happens), and New Vegas is more like a book: you read the lore and then it gets you thinking, and if you wanted you could have a philosophical discussion with other players about the ideas New Vegas presents. Problem is you can't have a discussion with a video, and yeah, a lot of the players don't give a DAMN about the game beyond shooting a gun. Hell, even culveyhouse was completely intolerant of Ulysses and unwilling to hear him out. (not saying he has to like him but at least hear him out)
Skyrim walkthrough could be fun, but I dunno if I mean that as a compliment. There's a lot of flaws with NPC interaction that are just asking for a comedian to make fun of them.
I agree, New Vegas is not good material for a let's play. The ideal let's play should have content that everyone has experienced so we get to see how another person tackles it, and their reaction. This isn't always the case the New Vegas, because there are so many ways to resolve things. One of the best let's play videos I've ever seen was TheRadBrad's Dead Space 2. Fantastic.
I always like culveyhouse's videos (the fact that he edits out load screens/lockpicking/looting etc really sets him apart, in my eyes) but I agree he was dismissive of Ulysses. I remember the huge sighs each time one of Ulysses' 10 minute monologues played through EDE. But I kind of felt the same way when I did Lonesome Road. I mean, I listened to everything Ulysses had to say (it was LR, after all), but even by New Vegas' standards it did go on a bit. It was interesting and all, but it could have been shorter.
I would LOVE to see GameplayJenny do a Skyrim walkthrough, probably for exactly the reasons you mention. There's so much comedy potential (bandit with an arrow in the face running towards you, anyone?) and awkward NPC encounters that GameplayJenny would be a riot.