Bingo!
Page 168 of the current Visual CADD user manual (
https://www.visualcadd.net/download/v9_user_guide.pdf ) talks about older plotters such as yours and how to bypass Windows drivers to print direct to device. It also advises to check your settings on the plotter to make sure that your plotter is configured for
hardware flow control.
Let us know the plotter model and we can look up the user guide for that and let you know what to change if it is still not working. It also talks about setting up a custom printer profile and what commands are needed to plot etc. Probably a bit too complex unless it is clearly documented in the Roland manual, or has been posted on the user forums where somebody else has solved this very problem.
I'm not sure if your previous Visual CADD configuration settings on your old computer were backed up. If so, it may prove useful to restore them to your new one, have a look at what they are, and take it from there.
This may be your easiest solution.
Windows 8x? Run, fast! Windows 7 or 10 are stable and fairly reliable. Avoid Vista, 8, (or 11 for now until it goes through some more beta testing on real users in the real world and has the bugs ironed out)