I still have 98, NT 4, 3.51, 2000, OS/2, and Mac OS here. The main reason to run 98 is improved game or driver support; compared to 2000 its Plug n Play implementation is embarrassingly awful, and USB support far less stable. Mac OS 8 is similarly flawed – whilst some functionality such as Quicktime feel impressively modern multitasking is non existent, it feels like an 80s OS.

The lack of USB support in NT 4 was starting to bite by that stage, however. The one thing you can thank the iMac for is killing off floppies.

By the late 90s Windows NT was starting to be the only viable way to run a solid multitasking operating system with a grown up file system, mainstream application support, and some games. Mac OS was flawed. OS/2 was barely alive (I switched to NT4 in 1999). Unix application support was limited and required a lot more work than now.

Favorably. The issues with 9x were architectural, and the same all the way to ME. Inter-process security didn’t, and couldn’t, improve on that architecture. MacOS was even worse, with most processes operating entirely in the same address space until OS X replaced it entirely in the same way NT did 9x. The subjective experience of stability between MacOS 8-9 was about the same as Win95-ME, though, I would posit both because developers on that platform had a lot of experience being very careful, and because, as a niche market, most software was paid for, which tends to up support expectations (and these were the days before open source took a society-wide hold)