Why are my purchases not being succesfully transfered to another library

Hi,
My Dad gave me his old Ipod nano 4th which contained a different library. I connected it to my computer. I then attempted to transfer the ipod's music to my library; by clicking transfer purcheses. I did however need to use his password in order to authorize my computer for that device. It accepted the password and the music began transfering from the ipod to my main library. The problem; it did not transfer all of the songs. My ipod has 764 songs, 2.2 days worth of music. My computer has only 529 sons with 1.7 days of music. I also confirmed that some albums were not transfered just by flipping the screens to check. How can I make both my Itunes library and my ipod have the same music/library.
Thanks and any info would help

Any error message provided when selecting import with iPhoto?

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