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Also jEmplode in the transfer tab window is saying there's modification to two of my paylists pending whilst it's hanged. I suspect this may be related. They can't be cancelled.
On a working system (such as you're friend's Windows PC), dig through those playlists and look for tracks or tags that are somehow unusual. For example, tags which contain non-english characters, tags which contain huge amounts of data in the fields (such as lyrics in the comment field or some such), or songs which were recently downloaded from the internet as opposed to ripped yourself.
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