I have a ruby script under OSX Leopard iTunes that will export a "folder" ( of playlists ) to a directory ( of symlinks and files ) that I can then rsync to the tablet. That combined with an iTunes plugin to re-randomize random playlists it works great.

Unfortunately canola has been a real disappointment for me since it STILL can't open a number of unencumbered AAC ( .m4a ) files that are playable in the default media player. I reported the bug back in the beta 5 days and they still can't find the problem.