Itunes not syncing all files to ipod - permissions error

With the newest verison of itunes is not syncing all of my files to my ipod - this is so frustrating! I have taken itunes/quicktime completely off my dell and reloaded with the newest version of itunes/quicktime. Changed to manually managing my ipod files. Now I have 2 problems left - 1. 2 recently purchased audio books show up in my ipod file in itunes but do not show up on my ipod; 2 I can ony get 100 of 500 songs to load onto the ipod with a warning that I do not have permission for the rest.
Dell Inspiron 9300     Windows Vista

Same problem here, same application versions. I'm trying to get them to sync to an iPhone but it doesn't actually sycnc. They play without issue in iTunes. I converted them from flac to Apple lossless using dbpoweramp.
Any suggestions would be helpfull

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