Caesar was a follower of the apocalypse and thus had access to a lot of old world data.
Including history, as he has modelled his empire almost seamlessly unto that of the old Romans.
(Though he could have had use of a few more books on latin grammar.)
The legion are by far the superior tacticians in the game of New Vegas, aside from mr. House who is essentially crippled unless the courier intervenes.
No matter his education, Caesar has proven to be a tactical genius.
Their shock and awe conquer tactics, their burning of resisting settlements coupled with the cruxifictions..
Its only a mercy in game they arent real cruxifictions they are only bound up there.
This is exactly the reason the Romans conquered Europa. Nobody dared stand up to them for a long time after what happened to those that did. No organised resistance.
New Vegas Caesar ruthlessly and mercilessly exploits human psyche to build an empire.
In my mind he is evil and he is insane, because he is incpable of seeing people as something other than things to be used.
He is a sociopath, and his empire emulates this by being sociopathic.
Would they win?
Hell yes.
Except these aren't combat tactics bro. Caesar being a Follower is only more of a reason he wouldn't understand modern tactics, I will say that I don't think he was typical Follower, in that he enjoyed learning about war and likely picked up tactics, but his knowledge of warfare is nothing compared to a group of people who decscend from the U.S. Army. The Brotherhood is trained to fight battles. Their knowledge on the battlefield is one of their greatest assets. They are expertly trained in combat tactics-all of them. While the Legion isn't, only their commanders-and that's said in game. As i said before, none of those things you said are combat tactics...The Brotherhood would completely outstrategize and outmanuever the Legion on a battlefield...As for morale tactics...which you listed...How is putting on Brotherhood soldier to a gruesome death going to lower morale on the same level that an absolute slaughter of a Legion company would? Such heavy losses consistently would take a huge toll on the Legion's morale..
If you want to find Legion strength's in combat, you aren't going to find it in the mental aspect of war. The Brotherhood is far superior in that aspect as well, as is their tech. All this is why I said the only choice the Legion has is a full out bull rush, in which they would lose thousands-because it's all their good at. It's their only choice, because their numbers are their only advantage. If they try to fight a war any other way, they're going to get massacred....Which isn't too far from what they'd be on a suicide charge anyways..