VM's are a hard one to set up if the program has to run native instead.
As for Mac, I have Mac High Sierra set up in VM shell using VM Workstation under win 10, and the glitch with it is printing out from the shell.
Hence have a HP 1100 that I use since, and there is no Mac native drivers for the printer, so have to use the VM's generic tools ware driver to get me out of the shell to the printer isntead.
My guess is your having the same problem with macOS virtbox as well.
If such is the case, then some times it just a matter of setting up the machine for a dual boot isntead.
If your on a mac, Book camp will set up for a dual boot, and the program should have no problem running on win instead.
If DD cut needs to run in 32 bit, then you can boot camp up a 32bit version of windows for the dual boot instead.
As for home CNC machines, I run Mach3.