Itunes freezes everytime I try to manually updated my ipod nano

Whenever the ipod updates automatically the sync works but I have too much music to fit on the ipod and therefore I need to choose the songs I want on my ipod but everytime I try to manually pick the songs and then click apply it starts to sync and freezes. I have the most recent version of itunes (itunes 10).

Similar issue was discussed here.

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