This is miserable and a poor design flaw. If someone downgrades delete their downloaded music, if someone cancels delete their downloaded music. For those of us who pay money to have access to offline music it's idiotic. YouTube doesn't ever delete your downloaded videos until either you do it or you cancel your account. I live where there is almost no internet connectivity and I've spent an enormous amount of time cultivating playlists so I can listed offline where I live. Your service as it is has become almost useless deleting my playlists as I burn all my limited satellite bandwidth to redownload every month. You guys need to reconsider this is thoughtless.
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I have the same issue so I'll see if my info will help Tanner. Playlist has let's say 350 songs I hit shuffle and within 20-30 songs I'm getting repeats then in the end it never expands outside of a hundred songs max. Meaning you never get to hear all the music in the playlist and the repeats are at a point annoying. I would recommend a function adjustment by the dev team that says the random pics only come from the yet to be played/unplayed items on the list as the listening session goes on and it should remember that and randomize/shuffle the remaining songs until the playlist is complete then start shuffling the whole list all over. We spend a lot of time curating our playlists with songs we love we actually want to hear them all and in a more creative way than listening to them in the same order.
I would love for there to be a shuffle function that says randomize songs not played until it exhausts the playlist. I've been working in computer development for 6 years I know this isn't a difficult thing to do. Simple logic that would actually shuffle to hear an entire playlist before repeating.
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