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.
Used ophcrack back when I was a teen so i could learn my parent’s windows password and fuck around when they were asleep. Then I figured just using live cds was cleaner (no browsing history to delete). Then once they upgraded, I was given the old pc to nuke and pave as I saw fit. It was a lot of fun outsmarting my parents in the wee hours of the night, not that they were terribly tech savvy.