Smart Playlists vs. Bookmarks

I’ve been trying to think about this to see if it will solve my listening problem. I’m not sure if it can though. Correct me if I’m wrong.

Here is what I want to do: I want a SPL which plays “works” (ie, multi-track pieces, so identified in Roon), which have not previously been played, from a specific genre. I want a random element here, so that the music is not all coming from one album.

I get part of this result if I go to genres, and then hit shuffle for play. It will randomly pick music, and if this music is correctly identified by Roon as part of a “work”, it will usually play the work, and then randomly shuffle to another “work” which contains multiple tracks but is not an album, of the chosen genre.

(Note that this only works part of the time, because many of my works are not identified as works by Roon, and so I still get a lot of individual tracks. But still, it does partly function correctly, showing that in principle Roon can do this!)

It does not seem to me possible to to set up a SPL that replicates this behaviour, and also includes the “play only works that have not been played before” desiderata. This can be done for tracks, or for albums, no problem. But not for works.

I had thought this might be solvable by using compositions, but there are two problems with this as the system stands. First, there options are not available in focus. Second, it is not clear how you would get Roon to appropriately deal with the “unplayed” request. Let us say you have 5 very different recordings of Composition A. How do you prevent Roon from thinking that just because you have heard one of these, you no longer want to hear any of them in your playlist? Hence my distinction between “works” and compositions in this discussion… (and thanks to @BlackJack for helping me see this issue).

Collective wisdom welcome!!