There were a lot of drivers who will not work with new windows versions. Due for examples of changes in things expectedv in the inf file or the registry. Installing drivers in windows was a lot of pain.
Ok, but again when you talk about "new windows versions" you're talking about an event that happens very infrequently, and most drivers do continue to work for decades without needing to be updated across multiple major versions. Windows 7 drivers from 11 years ago generally speaking still work in Windows 10 today. Hell, even Vista drivers (14 years ago!) often still work. Contrast that with the Linux kernel where you have to recompile external drivers, what, every few weeks?