If we can get your help, we will fix this. Sorry for the trouble.
I'm more than happy to work with the team to sort this out.
At this point, I have successfully synced MC with a folder on my PC, and did a simple manual copy to the device. So, my handheld has all music and playlists I need for now. This means I can stop using iTunes and my ipod. A great milestone!
I'm not at my PC right now, and don't know how long it will be before I am, so I'm not able to work on this for a couple of weeks.
Ideally, it would work just like the ipod/iTunes - plug in the handheld, use the point-and-click UI to tell MC what to put on the device (or just leave the settings as-is), hit sync, the software figures out what to transfer, and unless there are a bunch of music files to transfer the sync happens very quickly since it only changes the things that need to be changed.
Of course, Apple had the luxury of only dealing with their own devices (and the player software) so dealing with different android devices and the various players is a taller order.
For now, the sync to local folder and manual copy to device is working for me. It would be nice to automate it, and when I get back to my PC I'll look into that.
Big thanks to everyone who helped me get this far.