How can I share a few of my songs on itunes with another pc

I have sent a song from my pc to my sons pc and signed into itunes to authorise it on his pc with the understanding that this is allowed on up to 5 pc's. I upgraded his itunes and plugged in his nano. All appeared to be fine and his nano updated - but when he went to play the song on the nano (which was showing) it didn't play - in fact if defaultled back to the playlist. what have I done wrong? Thanks to anyone who has any dvie. SM

Either the SC folder in itunes or the ipods DB file is not taking the request or is corrupt.
Goto advanced>deathorize and deauthorize the PC for YOUR account over and over til you get "This Computer has not been authorized"
Then do the same over and over WITH YOUR SONS account/ID til you get "This Computer has not been authorized"
Now go here to delete the hidden SC folder, the artical is for itunes not opening after an update, but the steps for deleteing the hidden SC folder is the same http://docs.info.apple.com/article.html?artnum=302386
Once your done with that update the nano then disconnect it from the PC.
Play one of his sogns to authorize the PC again with his ID. Then play your song to authorize his PC with YOUR id.
Now connect the nano to the PC and update it or let it update if its on "Auto Update"

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