Idunno I feel like most of the arena games did a decent job of holding your hand and providing a single player campaign that is good enough to level up skills with a bit. Also back in the day there were a lot more LAN parties, and with the dominance of server browsers it was easier to get into a community that was at a suitable skill level.

But that does mirror my experience with newer games... the matchmaker usually isn't very good and I'm always put into games with players greatly better than me until I git gud.

In Dark Souls, other than a couple bosses which require playing reasonably well the whole way through, most enemies only have a couple gimmicks. You die to that gimmick once, go recover your souls, and then beat the enemy. There's a concrete sense of progress. Humans more likely have a pretty big bag of tricks, or just better fundamentals and map knowledge. I mean over the course of a game in an arena shooter, you'd probably just get incrementally better, right? It is unlikely that the top scorer of the leaderboard only had a couple gimmicks that you have to figure out and then win, haha.