I think Freeside was done dirty. It was supposed to be a lawless city that sits on the outskirts of the most wealthy casino resort but by the time you get there in the stereotypical playthrough the enemies that ambush you are very underpowered compared to you. It doesn't help that a lot of Freeside quests are just: "walk to this person, walk back, rinse and repeat." If Freeside presented more of a threat to the player then the Followers wouldn't be so pathetic.

I dunno. Fallout New Vegas is above all else a power fantasy. You are the guy who is at the center of everything and it is your actions that decide the fate of the mojave. What kind of gangster would they have to have in freeside to be any threat to the player who has already crossed half the mojave?

I do also just very much enjoy the breadth of content that you get to as soon as you enter freeside. There's just tons of stuff to do, even if a lot is fairly linear in execution. Just giving rotface caps to hear rumours about the town, or even just donating medicine to the followers is pretty satisfying. It's also just hilarious how they try to do this gritty gangster noir type stuff when the game looks like this: