I have a huge library of music, all nicely tagged using MediaMonkey. All metadata, including album cover art, is embedded in each of my FLAC files. As with my movies, all my music is in a single (big) folder - I don’t fall for the one-directory-per-movie/album thing as being harder to maintain. Plex doesn’t seem to pick up the music cover art when listing out all of an artist’s albums, which is a shame, and I think it ought. So all my AC/DC albums have the exact same Clan of Xymox cover art, which is most definitely not what’s embedded. Thoughts?
Is it really harder to maintain? I don’t think so. I personally buy music via Itunes or Amazon. Even if I rip a CD different applications always provide a dir/file structure exactly as Plex requires automatically. It is no coicidence but simply reasonable to have a minimum of structure to be able to find things that belong together on different levels (application level / file system level). I would even dare to say it is more effort to break this given structure into what you currently run with one large folder. Actually with a tool like mp3tag and a nicely tagged library like yours it is pretty easy to create such a structure with a click of a button.
And yes I could perfectly imagine the issue coming from using just one dir. Had similar issues before with a few albums in my collection. Either it was incorrect tagging which simply happens in a large collection or issues with folders / files which I didn’t detect because different application behave differently when dealing with such things.