From what I can tell, “shuffle” is currently limited to artist, album, and playlist. For me, this limitation is the biggest concern and inconvenience I have with Plexamp.
It essentially discourages me from building a varied play queue, as a result, my music listening experience isn’t as colorful as it could be.
Use case:
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There are times when I want to quickly build a play queue consisting of various genre/mood/artist/album/etc. and have it all shuffled for the listening session.
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This can kind of be worked around by having a playlist “Temporary” where I add songs to, although, that itself is quite inconvenient. It’s especially inconvenient as it’s not possible to remove all tracks from a playlist in Plexamp. It’s not possible to create a new playlist either.
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Let’s say I’m currently listening to “Go to bed” playlist and want to add several other songs to the play queue for just this session. If I did that, I’d end up with a fixed order for the newly added tracks while the rest are shuffled.
Just to have it mentioned, smart playlists are really useful, but it isn’t able to cover these cases, unfortunately.