So I spent a lot of time looking at the options and playing with different scenarios. I settled on the approach taken by @Craig_Palmer (although I greatly appreciate and tried out @Tony_Casey’s methodology as well). In trying Craig’s approach, I moved all 9 discs into one non-watched folder on my NAS and did a crash course in Yate largely for the ease of Roon integration (Barry at 2manyrobots.com was also very helpful). I made all the changes and then in Roon: Setting → Library → Library Maintenace ->Clean up Library, before moving the album back to my watched folder.
Here is what my NYA looks like in Yate:
Info Tab
Roon Tab
I added “Disc 1 - Early Years (1963-1965)” and the unique disc name in the “Work” field, preceded by the disc number so the results would sort in disc order:
Roon Results
So strange. Only two of the discs were clustered (see second image with disc 1 and 8) and it didn’t contain the “Work” break in the track listing. The others are split out as if they’re different albums (but with the same album cover).
dBPoweramp
For a different view and one were I am a bit more comfortable, here is the dBPoweramp view of the entire box set:
Looking back at Craig’s Box Sets B-52s vs Grateful Dead, I see that Craig added the full “Work” title and wonder if that may be needed to make this work:
I also wonder if there are still some things I need to do in Yate that I don’t fully understand.
Any thoughts on how to proceed?