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.
--------------------------------------------------------------------------- Your bitterness, I will dispel
Your problem was the main reason why I uninstalled iTunes and downloaded a program called "4VideoSoft iPod Manager" to manage files in my iPod. The only sad thing is that it removes all the album art, and the added songs don't show up in your total songs/vidoes count (Read the word "COUNT", you can still access those files in your iPod).
So I suggest you download it. Its not for free, so you have to pay for it. But you can freely use it for 15 days, I think.
And yes its legal and does no screw up your iPod. I have had no technical problems with it apart from the bug I explained before.
[Edited by HonestGamer, 7/8/2010 8:01:56 AM]
Why would you pay for something you can get for free??