For your first example if you use the classical Roon Work tag to name your cds and duplicate your track names as classical Roon Part tags you will get exactly what you want. You have to do a bit of meta date Kung fu to add these tags but it would look like this:
You would have a single artwork for all the discs which is appropriate in this case.
In your second case it would be better to break them all into individual albums so Roon could identify them as such with their own original artwork but add an album RoonAlbum tag to all tracks identifying them coming from the Original Album Series Box Set so you can see that is where they came from. It would look like this:
I used RoonAlbum tag to tag the CSN tracks as Box Set.
Takes some work to do this but would fix your issues IMHO.