After a lot of back and forth between MSDOS/Win98SE (I used to play a lot of QuakeWorld which did not need much), I finally got an AMD Duron 800 around 2000, and someone recommend me Win2k. It was a really stable system, way ahead of its time in terms of user management and services compared to Win98SE and early XP. I think I’ve stayed on it well past it’s final release. I got sucked into WoW in 2008, so definitely had to move on by then.