Belay my last!! (sorry military talk). This data acquisition is what is known as a General Purpose Data Acquisition System (GPDAS) and was orginally written as a DOS system. There is no Windows support.
I
DOS to USB all the time. That in itself is somewhat tricky but not difficult if you understand DOS, config.sys & autoexec.bat
Unfortunately, you're not USB to USB, you're USB to USB to RS-232.
There was a thread here, not too long ago about
USB for DOS. Search this forum and Google the same.
The adapter shown will require Windows, DOS support does not exist. If you can "force" it to work under DOS is unknown. You'll probably have to buy an adapter and attempt to make it work under DOS.
I'd say
dilemma is an understatement.