I got a question about the ipod 80 GB?

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Jul 2, 2008
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My Itunes library has over 5000 songs already in it, my question is when i 1st purchase the ipod and transfer the songs, in it Will it transfer all the songs or will it skip some of the songs. Or should i clear the library [not erase the library] and restart in putting the songs in the Itunes library and transfer the songs that way instead?
I have a Mac OS X 10.3.9 computer, so can someone give my any advice on this?
 

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