Did anything come from this question? I’m in the same boat after importing many iTunes-managed playlists into Plex. The sort order doesn’t match the way the playlist is sorted in iTunes and is honestly rather random: grouped by album, not grouped by artist (meaning that all tracks from one album by an artist will be together but tracks and albums from the same artist appear elsewhere), and not sorted by artist or album.
If I want to start shuffling a playlist by one song it’s basically impossible to scroll through a huge playlist to find it out of order, and searching all music only takes me to the source track, not the location of a track in a playlist.
Would love some option to sort playlists in both the web and iPhone GUIs. In the web I’d like the ability to sort playlists in the same way I’ve previously asked about within library artists:
