The one thing I couldn't make work right upgrading to windows 10 was the Microsoft webcam. You could almost force it but the quality became crummy. The one thing that broke in xp was my Microsoft joystick.
I think I remember reading some weirdness about legacy joysticks, because they didn't map cleanly to MS standard controller types or somesuch, so all had to have hacks in the drivers to be functional.
Which then expectedly exploded whenever MS shipped a new Windows version.