1) Caesar's absolute control of the Legion with no plans for succession or a Legion without Caesar.
According to Boone, Caesar actually did establish a full line of sucession. The issue, according to Mister House, is that this isn't necessarilly gong to be respected given they're a group of backstabbing tribals who aren't nearly as into the Kool-Aid as Caesar thinks they are (the Centurion at McCarran Airport for example). Disturbingly, killing Legate Lanius may help the Legion in the long run as it moves it down the food chain to possibly someone more visionary.
2) the Legion's support of slavery and the effect it has on the economy by keeping labor out of the hands of freemen (arguably the heart of abolitionism in the American west, see Free Labor or Free Soil movements)
Oddly, if Caesar were said to be DOING anything with the slaves (ala Lord Ashur) then he might have even more support. Rebuilding civilization or, in the case of the Legion, just building civilization period requires a lot of cheap labor. Slavery could well serve the Legion in constructing cities, digging wells, and generally making the East into a place worthy of life.
3) the degradation of women in Legion society and how that affects its popular support in areas that are not currently but could be soon members of the Legion (specifically New Vegas and the NCR west).
I, personally, wonder what Caesar's reasons for this were. Was it due to the tribes were naturally sixist to begin with or does Caesar have an agenda? Or is Caesar just a misogynist [censored].
For example, from Cass' dialogue it would seem she is a lifetime supporter of the NCR but hates that she admires the Legion in a way that could be deeper or easier to embrace if not for their views and treatment of women, and finally 4) the Legion's, or specifically Caesar's, distaste for technology
In Cass' case, it's mostly just the fact that the Legion genuinely does bother to protect its caravaners, which is considered a non-issue by the NCR. I don't think Cass is in any way tempted by the Legion but is frustrated by NCR's overstretched and incompetant nature. Unlike Boone, whose issues with NCR is mostly limited to Bitter Springs.
Still, Raul's point that the Legion's territories were worse before the takeover implies a number of things. I'm inclined to think the rampant misogyny and slavery was probably already there - it's just Caesar is now establishing the beginnings of civilization. Probably working on moving the East from the Stone Age to the Iron Age to Medieval and maybe more if he can get more educated workers/slaves.
(Caesar's obsession with the White Glove Society seems to be based on the idea that he needs cultured "townies" so to speak to compensate for his Legion being nothing more than a horde).
It might be Caesar intends to conquer NCR in order to "reform" THAT society with his current Legion just a means to an end.
"truth, by all accounts it would seem all the tribes the Legion formed from and then subsequently absorbed were all at the same low tech level. Perhaps Caesar uses the low tech level not only as a philosophical unifier of the tribes of the Legion or as a method of control to keep some tribes who objected to their assimilation from using advanced technology and "liberating" themselves, thus keeping himself at the top and in control. Which leads one to wonder if Caesar truly feels his method of governance is better than the Republic he's trying to destroy or if he's merely a megalomaniac who holds a stranglehold on the control of the Legion for his own ends?
in either case, I feel Caesar's objection to technology on the grounds of that it weakened humanity and brought the nuclear holocaust is another example of either ignorance of some aspects of Roman culture or just revisionist history on the part of Caesar. Both the Roman Republic and Imperial Rome dominated the rest of the known world in technology and its application. If he truly wanted to emulate Rome he would be much more accepting of that fact."
I'm inclined to think Caesar is a megalomaniac who enjoys playing God. However, he genuinely believes he's a super-genius making the Wasteland a better place. The technology issue, however, may have a legitimate point. Scavenging technology has lead to a good deal of reliance on it versus actual industry and so on. It might be that Caesar is intending to reassert technology once he has control of Vegas and so on.
He just is keeping low-tech for his tribal legions.
I don't know why Caesar doesn't want the Securitrons at the Fort. If he really wants to win the Dam using his own men, that's understandable, but he should have used them to barge through Mojave Outpost and just run amok in California, killing as many NCR people as possible.
It's wrong to read beyond a character's words when there's no sign but it's equally possible Caesar just doesn't TRUST the Securittrons since he's not a scientist.