Very nice set up. I'm a big fan of Roksan equipment. A couple of points that may be relevent. I owned a pair of Vandersteen 2CE Signatures and a pair of Meadowlark Sheawater Hot Rods simultaneously while deciding which to keep. I preferred the Shearwaters sound; more lively while the Vandys seemed overly soft, maybe polite is a better word. Also, the Vandys were just to imposing physicaly. At the time I was evaluating these speakers I was using a Roksan Kandy III integrated with various cd players.
My next point addresses your question better. I am in the process of moving and have my system in boxes. Now I'm listening to a pair of HD-600s. Love these headphones. I am hearing so much more detail with these headphones compared to the system with speakers it's amazing. Last night I was listening to Annie Lennox and noticed instruments that I never heard before. I'm not sure how much of this sound can be heard in a conventional listening position through speakers though. Now there are some negatives such as reduced spatial clues and less bass. I suppose it's a trade off.
If more detail and spatial information is what you're looking for, I'd say look into speaker upgrade. Good luck.
