My online education started in earnest on Chicago-Land BBSes.
In the mid-1980s I hung around a lot in the pirate scene in Chicago (mostly BBSes located in the suburbs - 708), trading files and being paranoid. pirating "warez" was great because i had expensive taste in software that i couldn't support with money. i could download program after program, try it, use it; few programs stayed on my hard drive longer than two weeks. installing massive amounts of software is a great way to learn the user side of dos/windows/os/2.
Besides that, there was weird porn, anarchist-cookbook style text files, nearly unintelligable stories of hacker/pirate busts, much macho posturing. Great fodder for a young male imagination. I worked on a hacker newspaper, The Humble Review, since I couldn't program or hack, that was my (puny) claim to fame in the underground scene. i submitted an article on Akira.
I did design ANSI art screens for boards, and I was co-sysop of "Snarf's Music Studio" for a while. I mostly hosted the poetry forum there; a lot of anti-death penalty and anti-gulf war ranting, interspersed with fifteen year old male creativity. A few sites would only let you download files if you posted messages, or posting messages was a way to earn file credits. So I learned to participate in conversations online to support my habit. I could never supply anyone new warez releases with 2400 bps.
I called up a BBS in Chicago called the Dog House South (not to be confused with the Dog House North, another BBS). The experience was pretty boring until I discovered that I could break into the PCBoard sysop functions, including user records. I spent a few hours tinkering with the system, setting up accounts, and never called back. I recieved a phone call from the sysop three weeks later (since I'd put my real phone # in my user record, duh) and I was harangued for violating his system and increasing his workload. A downhome exposure to the ramifications of hacking.
Eventually, I was exposed to the Internet in 1990. While there wasn't so much warez, there was great information. I haven't really gone back to BBSing, only the occasional Hotline server.