Ulysses is interesting in that he
knows he doesn't have all the answers, and hates both the present and the past. He is a walking paradox, an anachronism. It is important to note that whatever he talks about, can be inferred to be a puzzle piece to his paradox. There are many such conflicting ideas:
-Ulysses hates the old world for what is brought to the present, and yet wears it's flag on his back as it saved him from death.
-He hates Mr. House for being a hollow empty being herding around empty beings with grand and hopelessly outdated ideals, yet acknowledges his extreme power of directing the events in the Mojave. It even sounds like Ulysses fears House the most.
-He acknowledges Vegas being a bastion of safety and freedom, but as House let the rest of the US burn to save his Vegas, so too he worries that, in time, House will let it happen again.
-He respects at least the Courier's power to bring death, even accidentally, yet knows the life that the Courier is implied to have fostered all over the West. He simultaneously loathes and holds kinship with our protagonist.
Ulysses INVITES you to Hopeville and talks at great length about history because that is his problem. He has lost his compass, his past, and disowns the present. His paralyzing fear actually leads him to believe anarchism is the best solution with the destruction of every major player.
This is a beautiful adage to New Vegas's theme of letting go and knowing your place in things. Ulysses can't let go of the FUTURE. He is cursed to be intelligent enough to know he is a Deus ex Machina capable of bringing a result. Quite simply the deliberation of such a powerful decision destroys him.
Sinclair at the Sierra Madre could not let go of his Vera, Dean Domino his obsession with his image. Christine can't let go of her emotional avarice. The NCR can't abandon their national pride.
Do I need to mention the BOS?
At least the Enclave of all factions had a real master plan and the means to execute.
Ulysses can never respect or pledge allegiance to one of the nations. He has exhausted his ability to care. But he CAN still place his trust in an individual, an individual who almost killed him, killed his home, and killed his spirit; an individual who strolled along confidently leaving destruction in his wake; an individual who met death and laughed; an individual just like himself, a person who really does still CARE and who has the POWER to bring change and legacy.