Windows ME was released a year before OS X, so that’s not really the era to compare. Also, Windows 2000 was pretty solid. Before Windows 95 there’s simply no comparison, the Mac was much better.
Classic Mac OS might as well be part of the 90s kid starter pack (Kid Pix usually is). Macs were ubiquitous in American schools.
It was pretty intuitive, especially if you grew up on it. It was also still fairly easy to trigger crashes and break things, but maybe not for more normal people.