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My beef with iTunes playlists is that the songs overlap by a few seconds at the end of one/start of the next when I play them. There's a setting to prevent this, or select it. I change it. Works for two or three songs, then changes back of its own volition to overlap.
I don't bother playing any play lists I create with iTunes ... but must still create them so I can download them to devices that don't exhibit such misbehavior.
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