Apple doesn't allow iTunes to import music from an iPod because of a deal they made with the RIAA. If he were to just attach an iPod to a computer that it hasn't been synced with before, it will ask if he wants to erase everything and start over, which he of course doesn't want to do. Luckily, it's not difficult to get around this roadblock. Mike will need a program such as Sharepod. This will not only import all the music, but will also include playlists and album art.