We've tried running it in a VM before, with no luck.
It is a utility for writing and installing routines on a programmable controller.
My next door neighbour uses it. He is currently trying to reprogram his down-rigger for his fishing boat. ;)
The software is proprietary to the controller chips and the programmer. It will only work off of the floppy disk, with the supplied programmer. We can get the programmer to work with an lpt to USB adapter.
I have been able to create an image that will write to another floppy, and still work, but no success getting it to work with a USB stick.
We have managed to get it to work with a floppy in Win7, and it did work in Win10 for about 2 months.
Looks like we are going to have to set up an old system to run it. It will be a faster solution than wasting any more time on it.
As it doesn't need the internet, it can be anything that will run MS-DOS 3.3 or later, and has a parallel port. I have an old 8086/7 that still works!
Thank you for the assistance and input.