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.
I’ve been a Mac guy since 1985 but I’ve always had additional machines running other OSes (including Windows). My first Linux experience was with Yggdrasil, which my small company was trying out. We never got it to boot. After that, it was early Red Hat, which I ran for years until the hardware I was using died. After that, it was various versions of Ubuntu on machines at work. Now I’ve got a couple of Raspberry Pis running Raspian.