I've been toying around with my Zune lately and it associated piece of crap software. I was trying to find a way to sync MC playlists to the Zune. No way to do it through the front door, but I found a hack which sucks, but does allow me to sync stuff from MC to the zune.
The only way you can get this to work that I have found is to first install Media Monkey. Media Monkey creates a playlist which is compatible with the Zune. You don't have to use the software, just download, install it and fire it up one time. This creates a playlist called MediaMonkey in Zune and Windows Media Player.
Now here is the crappy part. Once this playlist is setup, you can take the playlist items in MC and drag and drop them to Media Players Playlist. If you then add these files to the MediaMonkey Playlist, they will magically appear in the Zune Software. Once that has updated, you can now sync. Unfortunately, if you try to sync another playlist, it does not overwrite the stuff that has already been synced.
Is there any way to find out how MediaMonkey is creating this playlist as they are the only folks that appear to have some type of integration here with their playlists.
Just thought I would provide some insight in how to get stuff from MC to the Zune, albeit, you need 4 pieces of software to do it, but does work in the end.