I doubt if Roland does much with Cakewalk on a day-to-day basis. Roland's direction has more to do with exploring synergies between the two more than anything. But Roland does have some responsibility for the overall direction that Cakewalk takes, they are, after, the owners of CW.
We're it up to me, I'd like to see CW rethink some of its GUI strategies. This isn't to say the the X series isn't a fine effort, just that are some things in Sonar's GUI that feel out of order. For one, the right-click menu system is all hit-or miss, you never know what you're going to come up with. I would think it's time to explore a more modern code-base, from what I can tell, it's at least 10 years old.
Now, excuse me while I go put on my asbestos underwear...