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.
Windows Vista completely died on my laptop back in 2009. I’d vaguely heard about this other OS called “Ubuntu” shortly before that seemed neat and was especially cool because it was free, but was too nervous about breaking my machine to try it before, but because it was already broken at that point, I had a friend burn me an ISO and installed it. I learned Ubuntu was actually Linux when I was configuring and learning how to use it, and that’s when I learned about concepts like FOSS, Linux just being a kernel and not the whole OS, and the idea of Linux distros. The only time I looked back was dual booting a gaming PC with Windows 10 for a while just before Proton came on the scene. Even then, booting into Windows was rare, only for games that did not work on Linux at the time, which with Proton releasing and constantly improving, became even rarer as time went on. A failed distro upgrade last year (likely due to me messing around with Mesa driver versions) finally had me wipe the Windows side from that PC altogether and go back to only running Linux when I clean installed over both Windows and the other broken Linux install. Truly haven’t looked back since.