Hi,
I scored myself a 4th Generation iPod on ebay, and as I use Ubuntu exclusively, tried to get it working with Rythmbox. I was able to create one playlist ('commute'), and get that to sync to the iPod, but it would not allow me to sync any other playlist.

So I tried gtkpod. That went well, and I was able to sync one playlist, but as soon as I created another, and tried to sync that, a warning came up, telling me that I'd be deleting the first, if I synced the second.

OK, so I installed banshee. That was better, I got almost my entire collection onto the iPod, but every song was duplicated. I checked, and there is definitely only one copy of each song on my laptop.

So, here we are. Can someone tell me if there is a program for iPod on Ubuntu which doesn't have these issues? Alternatively, it's entirely possible that I'm just not using the stuff correctly, and if that's the case, then that's OK, too.