NT 2000 was the one I used the longest. I’m still running a server with that operating system. It works great. Eight SCSI drives in two Raid configurations with a Dell Server with two power supplies. Good stuff!
for me it went:
DOS with automenue
3.11
98
XP
vista
XP
I was very late to every OS except vista, which I was an early adopter. I don’t expect I’ll be early to any OS ever again. Well, maybe to windows 9 I will. It depends how long it takes for them to come out with windows 9. I’d like to skip over vista, seven, and eight. I fear XP is going to be a relic in about 2 years. But maybe not, ya never know.