Mine has been doing very similar things since I took delivery of my 2015 Yukon. I specifically keep 160gb iPod’s in my vehicles as music servers. Both are newer than the 5th gen Classic. Both have about 85gb of music, and many playlists. Since day one, they have not functioned with the Intellilink. Always the same, plug in or start up fresh, it indexes, displays all the playlists, lets me choose one and then within 9 songs, it locks up both the iPod and display. Nothing plays, counter stops on screen. Only rebooting iPod clears it up. I had a major update done to it in January which did not resolve the issue. I get same on an old iPhone 4S with only 4,000 songs. My iPhone 6 with 128bg does better but 1., I don’t like using my phone for my primary music source and 2., even it will lock up, not be recognized (no USB device found) or it’ll start playing like the first second of the next song on random but then skip it and go to the next one. Sometimes skipping several in a row?
I’m going in for another update tomorrow that came out April 17. Hoping for some results. And BTW, my 2011 Maxima has no issues with any iPod I throw at it. Flawless. GM needs to correct this.