Probably, but I'd also wager that the majority of those devices use physical connections that any machine capable of running recent windows versions do not have

Probably, but I'd also wager that the majority of those devices use physical connections that any machine capable of running recent windows versions do not have. E.g. DB-25 ports. I will also wager that the only real "wall" that would prevent old hardware from working was the removal of 16-bit support from x64 versions of windows.