That's tempting for studio and live albums, but what about Greatest Hits where each track is tagged with the year it was a single?

Well, I'm talking about when you have a group of albums, and having it choose which album to play first. Not how you choose to play tracks within an album.

Agreed that Greatest Hits albums should have their tracks individually year-tagged (and I often go to the trouble of doing that myself by hand), but so far I haven't seen an example of that being the case in the CDDB. For the few compilation albums that are year-tagged, they always seem to be tagged with the compilation's release year.

Because even THAT isn't really the best solution for compilation albums, then you're right, there isn't a proper solution for compilation albums in that scheme.
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Tony Fabris