How do I transfer iPod music to iTunes libary?

I have had many problems this weekend trying to share music with my sons iPod. Having eventually given up on sending him the files I have been advised to plug his iPod into my iTunes and update manually. I have dragged the selected songs to his iPod and they are there!!! (surprise surprise) But now I want to organise them for him into playlists - so when I plug his iPod back into his pc and open iTunes on manual update I am unable to move any of the tracks from his iPod to his iTunes. I would really apreciate some help on how to do this the less complicated way. I have read in other postings that you can get a third party software to do it - but there must be an easier way to orgainse it. Any help anyone? SM

Hello and Welcome to Apple Discussions. 
Sorry to be the bearer of bad news (having had a look back at your weekend's postings ;~| ).
iTunes to iPod is designed to be a one-way transfer only. Apple has implemented this limitation as part of their Digital Rights Management (DRM) and their contracts with the Record Companies. To that end you have to use a third party application which is unfortunate because this is inevitable more complicated then if Apple had implemented it.
This post by Zevoneer has a good list.
kind regards
mrtotes

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