In my experience the first really stable Microsoft operating system was Windows 7. Win XP was a step in the right direction but I recall every 18 months or two years having to do a fresh install of XP as it became bogged down and sluggish.
I only used Vista briefly, it was so SLOW and didn't bother with 8 or any of its variants at all. Same with ME, I skipped that. There was another I didn't use either, what was that? 2000? NT? Can't remember.
I still have Win 98 installed on an old AMD Socket A machine just to play a few old games and I was actually quite shocked to discover how fragile and unstable it was, Win 98 gets upset and corrupts very easily. I can't remember Win 95 except to remember loading about a zillion floppy disks to install an office suite or a game.
Then there was DOS, earliest I used was 6.0, kinda like using the terminal in todays Linux Distros, you had to know what you were doing. It was, however, imo, more stable than Win 98.