Yes, I think we are coming at the problem from different perspectives. Most of my listening is in the classical realm (and therefore I tend not to listen to many playlists), where box set management (and metadata in general) in Roon can be a real mess. I do understand that discs have cover art and that tracks don’t, but that only highlights the problem with the example I raised.
Here is a prime example is my collection:
It’s a 22-disc retrospective anthology in which not a single disc corresponds to the contents of a single previous release, so assigning cover art from a previous original release to any disc in the set makes no sense (to me). I suppose through Roon’s “Fix Track Grouping” function I could “manufacture” partial individual discs so that their contents can be covered by one original album cover, but that seems like way more trouble than it’s worth.