I was talking about this with an office mate yesterday. He uses iTunes and hates the non portability issue too. For him it is the need to play them on non-apple devices. He now just uses bit torrent for most stuff.
Please explain what you mean about "non-portability." You can save your music, out of iTunes in any format you choose. Videos and movies, no. Those ARE digital rights managed because of copyright and rightfully so. . . but they can be watched on any Apple device owned by the user, so exactly WHAT is his problem? If he wants to watch it on his big screen TV, no problem. Want to watch it on his iPad, iPhone, Mac, iPod touch, no problem. But if he wants to give a copy to a friend, he's got a problem. That's illegal and he can't do it. That is NOT portability, that's theft.
Your friend can buy MP3s from Amazon’s music store instead. Then there is no portability issue, the songs are MP3 format, and he’s also not stealing. Amazon even has a little app to download the music and move it into the correct folder, add to iTunes. or whatever.