@Heron2318
Turned out it was an iPod issue - formatted and restored and issue has been resolved.

I've successfully added some music to my Gen 7 iPod Classic (Strawberry is the only one of 5 different options that has actually worked by the way!) and have found it's better when loading a few GB at time, to avoid an error message. The last time I plugged it in to load music on though, the player has become stuck on 'loading iPod database' and 'updating 0%' beneath the iPod icon for around 2 hours before giving up. I have relaunched a few times and tried launching from the terminal but it hasn't fixed the issue. Any suggestions?