My pick would be, dealing with the ‘wild west’ atmosphere. That being, before cyber bullying laws existed, you had bunches of people getting off scot-free with telling you to off yourself or call you a list of derogatory terms.
Hand-curated categories -> lists etc.
Think back to what Yahoo originally was. Drill down through categories, subcats, etc. to find what you’re looking for.
Worked for the time, but for a technical query today would be an absolute non-starter
I always thought the relative lack of people sucked back then.
Now I kinda wish it didn’t have as many.
The vitriol was more or less the same as it is now, though. It really was dependent on the spaces you hung out, and if they were actively moderated and had rules against such crap. All but one of the spaces I would spend online would have dropped the ban hammer on someone telling someone else to kill themselves or for using a slur/spouting hate speech.
But it was also easier to find spaces where that kind of talk was encouraged, too.
I was there way before “wild west”. Back what you could safely assume that anyone you met on the internet either had a degree or was currently on the way to get one.
But what I would miss mostly if transported back in that time is the complete absence of any search engine or centralized knowledge repository. Just imagine a web without google, bing, etc, and with no wikipedia site equivalent.
Our “search engine” was a hand-written notebook in the terminal room, where everyone noted down interesting internet services they had found, including the numerical IP address of the server in case the DNS was flawky.
The wild west part was the best part. It felt real. Now it’s all watered down.
It was also a barrier to entry. Especially to advertisers but alas that did not last.