with limewire all I did was click to my device in ITUNES, click recently added and boom sync, no problems. I manually added 2 songs and it shows to the left under my device but I cannot get it to sync for the life of me
I've never used limewire so I have no idea, but maybe you just don't have the complete file? I'd try downloading from elsewhere, converting to mp3 if required after the download, and then loading into an itunes playlist. The link kiwi posted is a great site.
Disregard advices if I'm not understanding you. I'm pretty clueless when it comes to this stuff.