All OSs have silly legacy-based limitations. The problems caused by this compatibility feature were just never frequent enough to warrant attention. Nowadays Microsoft has less give-a-damn for user suffering than ever before, so I suspect that this bug will be in Windows right up until Microsoft finally stops pretending to care about the Desktop and abandons it.
But it doesn't have to break anything. Programs written for DOS or old Windows version already tend to run in compatibility mode. You can have these devices be "everywhere" when the program runs in PC-DOS compatibility mode, and in \dev\ when it's not.