Is it possible to sync automatically on a Mac?

Love my new clip zip, but I have a Mac Pro and miss how easy everything was using my shuffle and itunes.  I still use iTunes since I can’t yet find another way to do what I need yet.  Speficially, I need some advice from Mac users:

  1. How do you prefer to manage your music? 

  2. How do you get playlists into your clip zip?

  3. Is there a way to automatically sync the clip zip on a Mac? I know iTunes won’t sync with non apple products, but I can’t find anyting else that will auto sync on a Mac.  Seems like that’s possible with Media Monkey, but that’ doens’t work on Macs.

Any help is greatly appreciated, thanks in advance.


Still no luck auto syncing with the Mac.  But Rockbox makes playlists much easier to work with.  Not sure why that is, but it works.