I’ll go first, I took my mom’s college textbooks which came with discs for a couple distros and failed to install RHEL before managing to get Fedora Core 4 working. The first desktop environment I used was KDE and despite trying out a few others over the years I always come back to plasma. Due to being like 12, I wanted to run my games on it, and man wine was not nearly as easy to use (or as good) as it is nowadays. So I switched back to windows until around 2015 or so when I spent the next few years trying to replace windows as much as I could. Once valve released proton, I switched fully and have t looked back, unless my still there windows partition tries to take over my computer when I restart it at least.
1993 or so with some Slackware CDs, i bought, because I had no internet back then. Took ages to compile, and never got past the black x on the checkered background when I tried to startx. Console worked nicely though and I loved the bash (?) experience with command history and all that. However, no games, very little software, and I didn’t program back than. It took quite some time to be able to use those things productively as a user.