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Interesting, I haven't had any of those issues with tagged media. I use beets for the tagging and sorting, and it's been otherwise fine? I do \music\artist - album for the directory paths, though, so it's already happily sorted and grouped correctly on the filesystem in a way that jellyfin seems to like.
Nice, I might give that a go. So instead of doing Artist/Album/songfile.ext you just have all albums in the same level? e.g. Band - Album1/song1.mp3 Band - Album2/song1.flac
If that's so, I might be able to batch sort them to that structure and give Jellyfin another try
Yeah, they're all a single-level deep. Multi-disc albums are also the same: artist - album/1-1, 1-2, 2-1, 2-2, etc.