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Difficulty shtting down IPod and reboot.
Difficulty transferring music from computer (PC) to IPod.
Help page does not address transfer from computer. Already have music on IPod, just need to update/add music.
iPod classic 160GB (Late 2009)
Here is a guide to adding content to your device: Manage content manually on your iPhone, iPad, and iPod - Apple Support
However if you're connecting the device to a new library iTunes may want to remove the existing content from the it. If so see Recover your iTunes library from your iPod or iOS device.
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How add music from computer to IPod?
