I think Windows 2000 was the high water mark. Compared to the NT based operating systems, the 9x versions were pretty rinky-dink in retrospect and not terribly reliable. 2000 was the best truly modern Windows that supported all the stuff we expect: NTFS, real user accounts, actual security, group policy management, the modern disk management utility that’s still in use today, the management console, native USB support (including 2.0 as of Service Pack 4), native ACPI hibernation support without reliance on janky vendor bullshit, etc.

Yeah, USB support. Everyone forgets that Windows 95 didn’t support USB at all out of the box and 98 barely accomplished it. 95 required the “OSR2 USB Supplement,” and 98 didn’t even support mass storage devices without third party drivers until the “SE” second edition. Those days really were that terrible.

XP was where the bloat really started setting in, but since XP was basically 2000 with extra shit duct taped to it you could still do all the same stuff with it vis-a-vis gaming and DirectX support, and by and large it could still use the same hardware drivers as XP even if vendors didn’t bother to officially support it.