Ipod manual sync issues

Why does my iPod not sync all the songs in a playlist when I manually sync it with my computer? It shows up as 51 songs in the playlist on my mac (all software is updated, included itunes recent version), but only 48 on the ipod playlist.

i know it sounds tedious but try and play every song on the list
if some of them give error messages and then show an exclemation mark next to them that means ur itunes still has them listed but the songs are not where the itunes thinks they are (them being deleted for instance) and thus does not actually have them to sync over. that would cause this issue.
if thats the case u should delete the songs that have those excelmation marks and resync. the playlist should be the same after that.

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