In 1999 I upgraded to a 486/66 (I think it was 66 MHz, or maybe 100 -- does that make sense? The Apple //e was 1 MHz). 200 MB HDD which I thought I'd
never fill up (lol). I think it came with 16MB RAM which was mind-blowing. I assume it came with Win 98 -- I did have a PC before that and ran Win 3.1 and Win 95 (and DOS). I never upgraded to Me, but my next computers did have XP which I used until just last year when I got Win 7.
Between '96 and '01, for 3 years in there I worked on a Mac at work.
BTW, I was using a GUI (graphical user interface) on the Apple // well before I got Windows -- I upgraded the mainboard to run
GEOS in the late '80s.