tracks not syncing properly

Hey All,

I have had my Ipod Nano 7th Generation for approximately 1.5 years, only recently started using it. Since I have started using it I have been coming accross an issue I just cannot seem to rectify. When I create a playlist that I wish to sync it does so without any issues but as soon as I properly disconnect my iPod and attempt to play the songs it skips over approximately 2/3 of the songs. It will show the name but will not play and quickly flip over to a new song.

I have tried uninstalling and reinstalling iTunes, resetting my ipod to factory settings, converting all files to AAC via iTunes. Aside from that I am not sure what else I could be doing. I am curently converting all the audio files fom a playlistto .M4A va another progrm to see if that will work.

Any help or suggestions would be useful. Don't know how much longer I will be willing to keep trying to get this to work.

-Jason