It's just weird that the mp3s will work on other ipods and on itunes, just not on the nano. Seems more like a tactic than a bug if you ask me.....
Are we moving towards the reality that only mp3s that came from itunes will work with ipods? Is apple assuming that mp3s that came from anywhere else are stolen? That is a bad precedent if you ask me.....
As everyone here has stated, there is nothing different with the music. It is true that the music you purchase off of iTunes is different that the music you are stealing off of Limewire. Itunes sends Protected AAC files with are actually MP4's, if I am not mistaken (someone correct me if that is wrong).
Regardless, this is not related to your problem otherwise your claim would be "My friend's nano only plays music bought on iTunes." The idea that an iPod only plays some non-AAC files and skips others is ridiculous.
The only explanation for this would be a corrupt song which has already been mentioned. While it was wrong for the Apple representative to lie to you, you probably had it coming. If you (or your friend) went into the store sounding like you do here, I probably would have told you the same thing. This... a) gets you to stop using limewire and b) is bs a person such as yourself would believe.
Go buy the songs and be happy. You dont seem to be rationally listening to anyone's advice. If you ask a question and get the same answer multiple times, it is not smart to discredit it. If you just do things the legal way, you will have less problems.
ps - I am expecting some sort of 'its not me, its my friend' response. Whatever. You posted the problem, expect a response as if you had the problem. I am not going to edit my reply to change 'you' to 'your friend' ...if it even is a friend.