however it sort of undermines the "insane compatibility" / "stable API" point if mass-market Windows software produced before the 2001 release of XP mostly doesn't work on modern Windows
NT effectively forked Win32 (introduced with Windows 3.1) into something incompatible
Current Windows versions trace back to Windows NT 3.51/2000 linage.
Naturally 9X => XP don't work flawlessly, they are two different OS stacks.