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.
My first disro was red hat 6.2 which wikipedia tells me was released in April 2000. I was fed up with Windows being crappy and crashing so I decided to try an alternative. Well, it didn’t crash like Windows did that is for sure but I spent a ton of time tinkering and upgrading and compiling. Linux has come a long long way since then. I have mostly stuck to it. I had a job that supplied me with a macbook for a while so for a few years I used osx, but I never fully went back to Windows. Now with proton making gaming more accessible on Linux I have no reason to ever go back.