The Roland CAMM-1 vinyl cutting devices are only supported up Windows XP, and best results are from the Printer LPT port on older systems.
Now you may have heard in forums that people have used the Windows XP drivers with the printer on Windows Vista, 7, 8 and even Windows 10 this is very possible using the drivers on the 32bit versions of these Operating Systems. Most people don’t have success because Windows 7, 8 and 10 are mostly the 64bit versions.
Here is what to try:
A computer that has a 32bit version of Windows installed
With a LPT printer port. (USB to LPT) adapters are cheap on Ebay.
As far as what software to use to design or send to the cutter, you’re have to do your research.