I was about to post in the #support category, when I found this response from @dylan to what appears to be the same issue being discussed here. Dylan points to this post by @mike who explains Roon Radio currently uses extra conservative matching at the track level rather than the album level. The idea is that it’s better to play a low resolution version of an exact track match than a high resolution version of a remix, demo or outtake of the track.
I understand the rationale, but I’m skeptical this explanation accounts for the kind of behavior I’m seeing. I cannot recall Roon Radio ever picking a track from my library. Which is why I end up not using it.