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 started running Windows 2000 in 1999 with a Technet Beta. It was fast, stable, reliable. Bought the new laptop with XP and it would hang from resume often. Then plugging in USB devices would stop being recognized and I had to clear duplicate entries out of the registry. Then my work desktop couldn’t open a second Vmware guest without swapping where it could run four guests under windows 2000. I burned one of my MS support calls asking them why it wasn’t reading the swappiness reg key only to be told they drop support for that so XP would have plenty of free ram but start swapping as soon as I tried opening the second vmware guest. I had to stick in another hdd and dedicate it to swap to get a second vmware guest just to run. But then there was the huge security hole thinly disguised as a web browser called internet explorer. Despite me running as a non-admin, file and registry permissions locked down, unnecessary services disabled, all the typical desktop security stuff just a simple mis-typing www.gogle.com into IE would result in popups and a malware infection. The second time I got infected bad enough to require a reinstall I setup a dual boot of redhat and eventually just quit using windows. Supposedly they fixed some of those issues with later service packs for XP but windows 2000 beta was faster, more secure and more stable than XP. It was just a big turd.