In addition to what Jim said, handheld sync in MC23 64-bit doesn't work at all. You'd have to use the 32-bit version if you want to use handheld sync with MC23.
Otherwise, see if you can connect the iPod to a PC and see if it's mounted as a USB drive with a drive letter. If you can, I believe the music files on an iPod are contained in hidden folders (albeit, they're named random characters, if I'm not mistaken).