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.
Oh gosh, it must have been 1999? 2000ish? I have no idea what distro it was or if distros were even a thing. It took me 3-4 days to get all of my driver’s working. I clunked along with it for a week or two until an update borked the system and I didn’t know how to fix it, so I went back to Windows. I tried many more times over the following decades, usually with similar results. About 6 years ago I really learned a lot more about Unix servers and therefore about Linux itself. So I installed it again and I’ve had it on at least one computer in the house ever since then.