Linux

The absolute best thing about it was that after suffering under Microsoft's shitty operating systems for years, you were running a Unix-like on your own hardware. That part was amazing.

I spent what felt like many moons trying to compile Gentoo when I was a kid. There was only the wiki and a gritty forum for getting answers, nothing in real-time. I didn't have very much knowledge of the kernel or messing with modules, and was certainly lost on getting a desktop environment going even after I got past the kernel part.

It was such an experience, I decided to become a janitor.

ETA: also this guy (not strictly linux, but same vibes)

stacks of diskettes, for every operating system.

would routinely spend hours doing an install only to hit a block and have to reinstall DOS to have modem access to get help on usenet. Then hours of reinstalling to move forward and repeat on another issue.

I really loved it though, it was a massive upgrade over DOS and windows on a 286.

The first time I ever used Linux was in high school around 2001-2002. I don’t remember what the distro was but it had drawing issues, clearly some kind of driver issue that I couldn’t figure out, on my PC so I switched back to Windows 98SE.

Not what op asked for, but it kept away from Linux at home until 2007. I started using Linux regularly in university around 2004.

I started using it before distros were really a thing. I got as far as having something that would boot to a shell, but then since I was 14 I had no idea what I was supposed to do.

Backed off until I bought a Slackware book that came with a CD. Then I had the fun of trying to get X working. Manually entering frequencies for your monitor was scary, because if you got it wrong you could damage the monitor.

Then I had a fun problem of either my modem would work, or my sound card would work, but never both at the same time.

Honestly I never got a system which I could actually use for anything, but I was a kid having fun, and it taught me to not be afraid of the computer.

Games: xbill, koules, and quake1 prerelease test(8 or 16 player multi)

Crafting XFree86 config lines to get a monitor working(no auto-detect for resolution modes)

Sharing tips, on how to solve all these issues, with others at Linux User Groups(LUGs)

My first experience was with two floppy images I found on "So much shareware! Vol.2".

It was labeled Linux 0.99b, no distro. It was not of much use to me at the time.

A couple of years later I got my hands on Slackware 2.0 on CD. So much time spent compiling your own kernel, because no modules and the whole thing had to fit in main memory (640kB). So much time spent fiddling with xf86config hoping you wouldn't fry your CRT.

Good times.

Then came gentoo, which had package management. No more did you have to browse sourceforge for endless dependencies to install something. No more did you have to re-install slackware on your root partition to update. So user-friendly in comparison.

We spent a lot of time on IRC.

MUDs kind of bridged the gap between IRC and games.

I remember spending a lot of time playing abuse, snes9x, quake + team fortress and quake2 + action quake.

Looking through music and budget software CDs at a computer store or a college vendor table, there would be one with a penguin or BSD mascot. It wasn't like the other discs that had DOS shareware games or utilities. The CD rom drives were 1x speed, attached to a card on the ISA bus, without plug and play, so it needed an interrupt number that didn't collide with other cards. The install process was curses based, with no mouse. There would be much time spent figuring out how to partition the drive, usually after buying a book. Back then, computer book sections were huge. The software install dialog had one line description per package, and it wasn't easy to tell what they did. Then there was setting up X Server and choosing a window manager. Not all video modes were supported, so it took a lot of trial and error with editing config files and resolutions before the the window environment would work. This was before home internet so it would take a weekend or all week to figure out. The only accessible communities in many parts were dialup bulletin boards, unless there was access to a college computer lab with a mosaic or netscape browser. At this point it was realized that I lived in a tech desert, quit my retail job, and moved.

Hard

94-95 school year for me. Prior to win 95. Honestly OS2 warp was the tits then, blew windows and linux away. But the cool thing about linux was that you could pull a session from the college mainframe and then run all the software off campus. Over a modem. Pro E, maple, matlab, gopher, Netscape, ftp/fsp, irc, on and on. Once you had X going on your 486, you were good to go.

But honestly, it was nerd sh$t. Dos was king until win95. And then nobody looked back until win8 made us realize Microsoft had started sucking.

Hmm my first linux distro was Suse 5.x that came on 5 CDs (i think it was 1998) ... can't say I used it much, I had weird German ISDN Internet at the time and the PPPoverWhatever (forgot the exact name) just didn't wanna work. Making music wasn't really feasible at the time. It mostly lay dormant. I slowly climbed the learning curve and switched to Linux full-time in the mid-2000s, when a lot more things were possible ...

We didn't have -R, you had to go into every subdirectory and run the command manually.

On the topic, did AOL work on linux? They were the google of their time, i can't imagine the FOSS world thought very highly of them

Why not just install an old version in a VM and find out?

But remember, no search engines for troubleshooting, forums and printed matter only. (And mailing lists and IRC, but they'd probably tell you to Google it, which is off limits for this exercise.)

I remember kernel panic and dependency hell. But it was also wonderful to get away from win95.

Imagine a pile of floppy disks, with stuffs inscribed on it that you never heard of....

... will you insert one into your computer and reboot it?