With Red, the ones that I never adopted as a primary OS
Windows 95 - It was horrible, but it was this shiny new thing, so we had to try it
Windows 95 OSR2 - Much more stable, actually usable, but still even mild hardware changes necessitated a full reinstall
Windows 98 - This one really worked well for me, so I kept it as my primary OS until XP
Windows 98 SE - I had all kinds of issues with this, never could get it working properly.
Windows 2000 - Game and hardware compatibility issues killed any chance it had
Windows ME - I didn't hate it as much as everyone , it wasn't worse than 98 for me but the bloatware was strong with it, so I never adopted it
Windows XP - Iinitally it had the same issues as 2000, but eventually after the first or second service pack it got good.
Windows Vista - The sloth of windows, you really needed 2GB of ram for this at a minimum, but it came out when many PCs were still 512MB
Windows 7 - I had some reservations about the UAC, and some UI changes, but eventually got used to them.
Windows 8 - this left me dumbfounded, when I first encountered it on a prebuilt, I couldn't find the most basic things in it, I felt the same way as I did when I saw a PC for the first time and knew nothing about DOS, I had to refer to outside help to get anything done.
Windows 8.1 - Too little too late.
Windows 10 - I didn't like it, but I had to go along with it, and for the record I still don't like it, and it gets worse with every feature update, eroding user oversight and control panel features.
Windows 11 - The windows after the last version of windows, I don't know why this even exists, it's terrible at best, broken at worst.