Same Problem - Reported Here - Fixed with new iPod
I had same problems repeatedly with iPod 160GB.
It is now solved... how? I had the iPod stolen and replaced it with a new one, re-synced songs and it works like a charm, no issues in 2 months. And it is instant.... before it took ages on the old one to recognise etc.
So my 'prognosis' is find a way to reset and re-sync your iPod (many forums for that).
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