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Songs Not Playing, "Unable to Play Song"

A couple months ago, when I got this app, all was fine and good, I could play every song while I was on Shuffle. When I used the free trial, same thing. But, about 2 weeks ago, I began to recieve these messages saying "Song unable to play", and would abruptly end the song 2 seconds in. Some songs just won't play at all, with no message, just nothing. I can't listen to what I want because it won't play, and I spend my skips going to songs I don't want to listen to or going to a song that won't play at all! It is very annoying and becomes a bigger hassle than anything. I tried to sync it, but it only copies Local files and a friends playlist. I want the songs that I have on my song list, not local files (may as well download my whole music library twice). Does anyone know how to fix this? I have pictures to show what I mean.

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