I can finally use gtkpod on my MacBook laptop, though it is not completely painless. This may be the last item that was keeping the Linux laptop around.
This was done by running gtkpod on Debian in a virtual machine running in VirtualBox, the ipod file system was attached with sshfs, and the destination where I copied the music to was also attached using sshfs.
First I made sure I could SSH into the MacBook, this was done a while ago and I can't exactly remember how to turn on the SSH server.
Then I installed VirtualBox.
Next I installed a basic Debian instance, and installed the openssh-server, sshfs, and gtkpod packages.
I ssh into the virtual machine with the -X option to enable X11 forwarding, make sure iTunes is not running, mount the iPod file system over sshfs, and launch gtkpod. At this point gtkpod is on the screen.