I'd say the writing is pretty bad on a lot of levels, which is why there's even a debate. You can do characters with off-kilter or odd beliefs and do it well without them seeming too pretentious about it. If Ulysses is just very angry and it poisons his judgment, you can portray that too. NV does this constantly with its characters. (Elijah, Joshua Graham, Dean Domino, God/Dog, Caesar and so on.)
Personally I find Caesar's use of Hegelian Dialectic to be a rather silly personal belief. He seems to believe, in practice, if not explicitly, that there's some historical inevitability to what he's doing that justifies his actions. It's a little pompous, but believable given the character. He's clearly very intelligent, but intelligence doesn't equal infallibility.
And actually Ulysses echoes a lot of Caesar when I think about it. Because Ulysses wants to wipe the slate clean with nukes. It's his own take on a kind of a conflict-based dialectic. There is no acceptable middle ground or compromise that can be built from what already exists. This is directly opposite Caesar, who places importance on the Legion and the NCR as its rival.
And Ulysses really does seem like he should be the warrior-poet archetype who would be brooding on whatever ideas he picked up from Caesar. Yeah dude does a lot of brooding.
Mind you, they don't have to come across as grounded in the reality of mere mortals. They're both bombastic and grandiose personalities. Fallout 2 pulled this shit off Hakunin. You could mock Hakunin for being a kooky old man who is hallucinating too much, but you did get the impression that he operated on some kind of internal logic that was knowable only to himself. Ulysses does a lot of that crap. He speaks in a lot of tribalspeak, similar to Follows-Chalk, just with a lot more mystical flavoring.
But for whatever reason, Lonesome Road just doesn't work.
A lot of it is that the set piece is this rather grungy and depressing setting of smashed concrete and storms. The place is just desolate and depressing. So that sucked to play in.
The Marked Men really aren't important at all. Nor are the burrow monster things whose name escapes me. They don't really have a lot of relevance to the plot. They're mostly pretty forgettable. At least Old World Blues, Honest Hearts and Dead Money had enemies that at least tied into the plot or theme of their DLC. (ROBO-SCORPIONS! ATTACK!)
So none of the enemies build up Ulysses.
You're informed that this destruction is the Courier's fault which just seems very shoe-horned. You'd think you'd remember something monumental like that. They don't even lampshade it very well. If you tell Ulysses as much, he just says, "Oh yeah, just believe me. This was totally your fault."
Well okay then.
By the way, we're also not shown what Ulysses lost. We're just told that there was some unspecified settlement in the ruins that we never see that was important to him. But no real reason why it was important. Just believe it when he tells you that it's the better alternative to the NCR, Vegas or Legion. There isn't any plot or setting element to show us. We're told. Also something about Old America.
So that pokes another hole in our investment in the plot.
It's hard to tell exactly what it was they were going for.
