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They crashed/BSODed a lot. A lot more than Winxp and later. Oh god how often they crashed
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That's because Windows 2000 and all later versions of Windows were based on Windows NT, which handled multitasking differently than previous versions of Windows. If I recall correctly, the older versions made it the responsibility of a process to release its control of the processor. That meant that if a program froze, it would freeze all of Windows.
WinNT had a seperate process that oversaw multitasking and forced programs to close if they had frozen. That's why the OS crashes less, even if the programs crash at about the same rate.