I don't have iTunes either. it doesn't run on my computer, so instead I have an open source program called GTKpod Ipod Manager. I would provide yu with a link, but I installed it via Add/Remove programs, so I don't have one. basically, you plug in your iPod, start the program, and creat the repository for your iPod (if you don't know what that is, don't worry it totally walks youthrough everything) and then you just import files/folders from your computer to your iPod. it loads them on basically how iTunes does, so all the songs show up fine and add to your song count. it's a free program. the only bugs I've had is sometimes it tells me that the file I selected doesn't exist. I just remove t and try again and it usually works. also, instead of "sync" you "save" after all transfers. the program should work with every type of iPod out right now.
You have to tell your friend to set his iPod to "Manually Update iPod" to do this. It will allow you to add any song from any library (there is a restriction on DRM songs in that you can only have songs from 5 different accounts assigned to an iPod). Also note that this option will disable the auto synchronization that happens when you connect your iPod to a computer.
This option can only be enabled on his computer.
If it's not a whole lot of songs, you could always just burn the songs to a CD and transfer them manually.
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