In 1989 a grown-ass grad student at our flagship state university tried to get my 14 year old friend to visit him downstate. (She told me all of this via a handwritten letter, mind you, but she was communicating with this creep - who wouldn't admit his actual age - via an early text only messaging system.)
I remember the 1990s as a weird free for all, but also very gate-keepery. Oh, and those chat rooms/IMs out of nowhere were just... not even a thin veneer of "normal people doing normal things." (I'm OK with that, but let's not pretend).
The 2005-2010 era was all about collaboration (wikis) and forums and LORD ALMIGHTY, that almost always ended as a shitshow. Highlights from my memories of one wiki mashup:
One kid from Slovakia faked his own online death, came back a month later and held a memorial for himself under the guise of a real-life friend of the kid. No one was buying it, and he lost his shit over the lack of mourning. It was cringe, but people were pretty mean about it.
Another kid from Louisiana (if you believed his bio he was 11 and lived in a trailer park) was attacked by two adult men for "trying to score contribution points" on the wiki... by adding valid information to the wiki.
-An unhinged person in the Philippines threatened me with death, violence, and the destruction of generations worth of my family. That threat was delivered with the added terror-inducing information that her husband was a "lecturer at the university."
-One of the site admin's/owners (a Russian dude who was the equivalent of Reddit's Spez), banned a guy.... this is so stupid and complex... mainly stupid.... I feel stupid just typing this out. It was Russian Spez's birthday and a few people on the forum wished him a happy birthday. (Myself included. I mean, have a nice b-day dude. Typing costs me nothing and maybe it'll dislodge whatever's up your butt.) Another guy on the forum (let's call him Derf) called us birthday-wishers "suck asses." Whatever. Anyway, Russian Spez freaked right the fuck out, banned Derf, and started whining in broken English about why it's unfair that we "think it's OK that people call him suck ass." And although I'm generally a nice person, I took this opportunity to call Russian Spez a thin skinned moron. (Seriously - I'm a 30 something woman and I'm not pitching fits over a childish taunt, but you are? And it wasn't even directed at you? To his credit, Russian Spez didn't ban me.)
-Was creeped on like it's 1989 once people on that forum realized I wasn't a dude.
-There were internecine disputes over formatting, where people in the US banded together to create a local standard that made no sense globally, people in the EU banded together to make standards that made a little more sense globally but pissed everyone in the US off because they preferred to say "Kentucky" vs. "KY", people in Finland created their own insular state of affairs and refused to enter a debate over site-wide standards, and everyone else around the world just glowered and waited it out.
-Then there were the geo-political warriors. There were people in Iran and Iraq who fought an online proxy war over whether the Persian Gulf should be called the Persian or the Arabian Gulf. There was some drama over the South China Sea that I never really delved into. A single man in the middle east made 200 sockpuppets to defend 20 meters worth of sand in the Sinai peninsula that defined the border between Egypt and I-forget-the-hell-who-but-it-wasn't-even-Israel.
That got into HobbyDrama territory, but the point is: Shitshow. Always has been.
People just sort of suck. And when their natural impulses towards suckiness run up against site rules? Shit gets lost. When someone calls them out it becomes a personal grievance. The lawbreaker becomes the victim.