>>95265 (OP)It's not just about the software being old, it's also about the demographics of the userbase. Like you said, the majority of the userbase is young, creative outcasts. That's another part of the "old internet" before every person on the planet started using it. 4chan for example is flooded with boomers that don't create anything, just point at the clouds and complain.
I'm 22 years old and I first got into imageboards around 2016. 4chan was all over YouTube back then, both as the "scary boogeyman" and the "based internet though guys". I knew about it, but rarely ever used it. The first imageboard I really started using actively was 8chan. I made friends with a guy on steam because we traded items in TF2. While he didn't explicitly mention anything about using imageboards on his profile, I could tell he was part of the "scene" because of his sense of humor / memes and general attitude. I wanted to show that I am "part of the clique" and complained to him about how much porn there is on non-porn 4chan boards. He told me that 4chan is shit, and I should use 8chan instead. So I did that, and it grabbed me much more than 4chan did. I started frequenting the /r9k/ board of 8chan, although I still mostly lurked. I stopped using imageboards for a period of time, but got back into them around 2022 when I found the sharty through the 'ru. I don't use this site very much anymore, in fact I use 4chan more than I use this site today. There just isn't as much OC here as there used to be, too low PPH, and too many autistic children spamming NAS coal. 4chan also sucks, but in a different way, maybe the opposite way. But at least on 4chan I don't have to wait 5 hours for somebody to reply.
Picrelated is OC I made for the site in 2023.