Firstly you need to understand that MB does not directly support iDevices. There is an iphone plugin that might help.
That being said, I have been using my Classic with MB for many years with only a minimal number of issues when I first started using it. The iPod does not have "letter" paths. You have to do a complete wipe, reset, and restore and let Apple set the paths. A key part to the success of syncing to it is the ios version.
See this:
http://getmusicbee.com/forum/index.php?topic=18506.0Also, here are the settings I've used. And note that I did -not- enter the paths. They should get picked up by MB on the first connection between the two: