OTOH, the company I work for has a customer that uses some ancient automation software to run an industrial plant, and that software uses dongles attached to the parallel port, and I mean the parallel port. Using USB-to-parallel-adapters does not work, and finding motherboards with parallel ports has become rather difficult. :-|
And yes, those parallel port dongles were even worse. I suppose you might be able to find a PCIe parallel port card?
These won't work either?
https://www.newegg.com/Product/Product.aspx?Item=N82E1681515...
Have you tried modifying the Device Manager configuration for the USB-to-parallel adapter to assign it the I/O port and IRQ traditionally associated with LPT1 (I/O port 0x3BC, IRQ 7)? Changing exactly those kinds of mappings are the whole (original) purpose of the Windows Device Manager :)
The other thing you could do, though, is just run the automation software in a VM, and map the USB parallel port to the VM's LPT1. It's the IBM z/OS philosophy :)
But as far as I recall, the software runs on DOS (for real!), and attempts to run it inside a VM have not been very successful, because the link between the software and the PCL is very timing-sensitive or something like that. FreeDOS did not work, either; I got to install MS-DOS 6.22 on a few machines two or three years ago for that reason. It was fun actually, but finding three floppy disks for the installation media was ... challenging. ;-)
> mkisofs -b dos622_1.img . > \temp\dos6.iso
something like this, will get you a bootable CD that'll emulate a floppy and get you onto that first disk... It's probably easier to do a dump/restore set of whatever it is you need to install, or just make a boot floppy to load up MSCDEX & friends so you can xcopy as another solution.....
Parallel ports aren't too hard to find, there is PCI cards you can find with parallel ports.. Now ISA slots on the other hand....
On the upside, installing MS-DOS 6.22 from floppies took less than 15 minutes, and the freshly installed system booted withing 15 seconds. ;-)