It's a lot harder to explain the whole "anarchy" obsession that shows up in the files, though. Maybe that kind of loser attitude would make you "cool" and "a tough guy" back in the 1980s and the 1990s. Or at least that's what the file authors thought.
The world was a different place back then. I was 7 in August of 91, too young to remember or have experienced much of the world but I do remember the culture of pre-9/11 internet being starkly different from that of today.
That would explain some things, then. Indeed, those writings have a lot more in common with the pre-Soviet "nihilist" movement than anything relating to anarchism as it would be understood today.
That attitude was indeed cool and definitely not loser back then. It was “anti-The-Man”, much like the Anonymous movement whenever that was... 10 years ago?
It's a sign of the times. The mid-to-late 1980s saw a very conservative shift in politics that continued into the 90s-00s.
Once the whole "anarchy" thing started manifesting in real ways (numerous domestic shootings/bombings) by the mid-90s it was pretty dangerous to be associated with.
The new web is commercial, monitored, controlled.
There is a version of communism that says that people should live in a local community that helps people who need it. As long as someone who doesn't want to live that way has the reasonable option to leave, this is actually pretty hard to object to.
There is a version of anarchy that says that all laws and taxes should be at the local level and furthermore that some localities might then choose not to have any, or only the most basic ones like a prohibition on violence. It's almost the same thing -- pretty hard to object to when people have the option to exit.
What they have in common is that they can't exist when you have a central government de facto prohibiting them. There might be some real efficiencies in a commune that has its own doctors, but that doesn't really work if everybody there still has to pay twice the cost of their own community's doctors in Medicare taxes. You can't have much of an anarchist collective if the feds are still arresting anybody who tries to sell pot brownies or break DRM so they can repair their own tractor.
So people have been looking for ways to shed the yoke of central power for a long time. The US was practically founded on it, both in terms of why the revolution was fought and how the constitution was laid out, but the forces of centralization have been hacking away at those foundations and doing what they can to destroy the "laboratories of democracy" of Brandeis for a long time now.
Is it really that surprising that people were excited about a then-emerging opportunity to potentially take some of it back?