I'm currently using a Mac iPod with my PC running Xplay. I got the mac one for a variety of reasons which I don't need to go into now. Plus, using XPlay makes it pretty seamless to go back and forth between the two platforms.
Media Jukebox sees the iPod in its CD, DVD & Handhelds section. However, moving files and playlists to it acts just like a typical hard drive transfer. This is not surprising as the iPods have a separate special directory for songs which it plays. The rest of the hard drive behaves simply as that, a hard drive. Obviously, XPlay and their Explorer interface utilizes that hidden directory. So, in the small amount of time that I've played around with it, I've used MJ8 to copy the songs that I want over to the iPod, open the iPod root directory, and copy said songs over to the XPlay/hidden ipod directory.
As I said, I've spent only a small amount of time playing around with all this. I would like to experiment more. I'm not sure if you MJ people are even interested in making MJ8/9 play with a Mac version of the iPod, but if you are, I'd be glad to report more of my findings here. As I think that MJ is leaps and bounds ahead of iTunes, I obviously use the PC for most of my mp3/music needs.
Anyway, that's enough rambling for now.