Cannot update nano from my 20g photo library

I have gone to preferences and checked off 1 playlist that has all my wife's songs for her nano. It will not allow me to update her nano with these songs. My library for my 20g photo has 2300+ songs. I have a separate playlist for her 153 songs for her nano. Help!!!!

hi Keith!
It will not allow me to update her nano with these songs.
are you getting any kind of error message? if so, what does it say?
love, b

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