iTunes music hasn't had DRM for a few years now. He just needs to copy his music from your library (iTunes folder>music) and paste it into the folder for his. If he's on a different computer just copy to a flash drive then copy to the folder on his computer. Point iTunes to that folder and they'll be there. This is how we did my daughter's. Once it's done you can delete his stuff but anything bought on your account will show in the cloud. You can easily just hide it.
If he wants them to show as purchases in his account then yes, he needs to do home sharing. Movies and TV shows still have DRM so if he wants those he will have to do the home share. We have ours set up so that when I redeem or buy a movie it auto transfers via home share to her account. Hope this helps.
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