I was reading http://www.gamesas.com/index.php?/topic/1205437-new-vegas-overrated/ which turned to a discussion of The Pitt's Ashur in comparison to the Caesar and the Legion, and it struck me that after several playthroughs I don't feel that I understand Caesar's motivations for his empire. What I've taken from his length dialogues (practically monologues) is that he wants humanity to survive, and has taken a "cruel to be kind" approach because he believes it to be the only method of surviving the harshness of the post-apocalyptic world. But, to what end? What Caesar seems to lack is a vision for the future.
Consider Benny: through dialogue he explains that he's opportunistic and power-driven. Benny's story of how he took control of the Chairman is anologous of his attempt to wrest control from House. His motivations are to increase his influence, to attain a more comfortable position in life and to undo what he perceives as an injustice in House taking control of the Strip. His base motivation is ego, which is why he explains his plan to the Courier when his death appears imminent ("it's called having a legacy"). He's a well-realised character with believable motivations and actions consistent with them.
Now, back to Caesar. Caesar does have a clear idea of what he's doing right now and in the immediate future, namely rolling up the south-western USA into his empire. His motivation (as he states it) is to ensure the continuation of the human race by forcing them into a competitive culture, thereby forcing natural selection to promote the strongest of the species. But supposing he conquers the NCR, what then? His general distaste for the NCR is understandable, as he sees it as a creaking bureaucracy which he feels is better supplanted with an autocracy to provide singular direction (this is fairly similar to his namesake's motivations). The problem is that he doesn't appear to have a greater direction; there's no indication of what he intends his new American empire to achieve once everyone has been absorbed.
Going back to Julius Caesar and the Roman Empire, even under Julius Caesar's control there was a significant segment of society who practiced intellectual pursuits: doctors, historians, artisans, etc. The Legion is neither shown nor described to have any of these. Despite Caesar's start in the Followers (or more likely because of it) there seems to be no education within the Legion of non-martial nature. The only Legion healer of any description in the game is a slave who learnt her trade outside the Legion. Moreover, they clearly lack any dedicated doctors as evidenced by Caesar's medical condition and his lack not only of treatment but even diagnosis. We don't learn of any Legion scholars, or even encounter any non-military personnel. This is somewhat excusable as the Legion force in the game is meant to be an army preparing to assault Hoover Dam, however none of the characters mention any of these things existing further East either.
So then, what of Caesar's motivations? His claims of altruism are overstated in the least, since we see explicit suffering within the empire (the slaves present at the Fort and Cottonwood Cove). He sees that there are faults in the NCR's leadership, but his solution is to eradicate what traditional social structures have reemerged since the war. Unlike Benny, he doesn't appear to be acting for his own comfort, since his tent shows little in the way of luxury (granted, a bed and chair surpass what most others have, but not greatly).
There appear to be two possible explanations for his march westward: either he wishes to fulfill a megalomaniacal urge to rule what remains of humanity, or he does truely believe that his new culture (what little of it there is) is the only way for humanity to survive and thrive, yet lacks the long-term perspective to realise such a culture will only serve to continue its own existence and eventually either stagnate or be usurped by another with a stronger vision. In either case, it's hard to justifiably support his goals.
