I couldn't edit my previous post (http://forums.ilounge.com/showthread.php?t=206075) so I apologize for creating a new one. Jiri from Mediamonkey has updated the iPod plug-in, it will only work with MM3.
>>Link (http://www.mediamonkey.com/forum/viewtopic.php?t=20845)<<

It would be nice to hear some reports, cause I'm putting off getting the Classic until MM works.
Note that the plug-in will work only with MM3, which is still in beta and you need a lifetime license in order to use it.

PS. How do I edit my posts?
PS. Now I see the Edit button but not on my other post.