you have to put them on a cd and then onto your computer, if you're trying to get songs off an iPod and onto a computer, it doesn't work, so stop trying
depends... if he bought it DRM (digital right management) will make it impossible to be transferred to any other computer (even if he paid for them... or maybe is because he paid for them) now... if the file is free (neither paid nor registered) all you need is a flash drive