I think that Ashur and his Pitt Raiders were better fleshed out as a faction in such a short period of time than Caesar and his Legion.
I don't think this phrase, "fleshed out" means what you think it does. Look at the amount of details available on Caesar's Legion and compare that to the amount of details available on the raiders of the Pitt. By any metric, the legion is more fleshed out than Ashur's band of raiders.
Now, you can think Ashur is more believable than Caesar, or nailed the whole "good person doing horrible things in the name of rebuilding society" angle better, but more fleshed out? No.
Personally, I think the Legion is a more interesting and intelligent antagonist faction than Ashur's raiders, though this really only comes up when you talk to Caesar and Ulysses to a lesser extent.