I'm not sure why you would record to a digital recorder when you have a daw that can probably do a better job,, not knocking it,, I did the same up until I figured out that DAW's can and do work better..
This:
"
a Cakewalk user for 15 years, i don't have any problems recording synced up to my PC" but your issue seems to be one of just that?
How old is the Roland? first thing comes to mind is it is most likely the problem.
It's tricky setting up word clock etc but you say you've been doing it for 15 years so I'll asume you know how to do that. I've synced a few things to Sonar and it always worked just fine if Sonar was the master.
Is the Roland the Master or the Slave?