On my main computer I have a fairly large music library that hasn't so much grown as it has accreted over the course of two and a half decades. Because it's significantly larger than the total storage capacity of my iPad I'm using smart playlist synchronization to store just that segment of music on my iPad that I like to listen to often.
However, since the update to 8 or 8.1 or thereabouts, for some reason the synchronization silently fails on a number of songs, primarily mp3s that were not purchased via ITMS or created by using iTunes to rip a CD.
According to iTunes on my PC, the songs in question exist (and play correctly when I ask it to), and are in the playlist designated to sync to the iPad.
According to iTunes on my iPad, the songs in question exist and are in the playlist... But according to settings->storage->manage used->music, they were never uploaded, and any attempt at playing them results in the iPad silently skipping to the next song... and the next, and the next, until it finds one that was uploaded.
(Since my usual method of listening to music involves setting the 'pad to random play, this explains why it took some time for me to realize something was wrong and why I'm not 100% certain when it started going wrong).
Does anyone have any suggestions as to what's going on, or where I should start looking? I'm rapidly approaching the point where "upgrade to an Android device" starts becoming an attractive solution...
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