Jon, I can remember back in the early days of Mac emulation of Windows…. Things could get complicated with peripherals.
These days Parallels ( there are other emulation progs) is so easy to configure and fast with it.
What ever you have connected to your Mac by USB can be used by the emulated Windows ( nearly always even without the correct PC driver as it ‘sees’ the Mac connection as its own).
I used Mac with Parallels for programming Massoth and ESU decoders using their programming modules and PC software.
I have Windows XP as well as Windows 10 running in Parallels, (XP for those old PC progs that I do not want to update!).
So don’t worry, just get a copy of Patallels to suit your current Mac OS … Which OS are you using ?