This worked for me.. Thought I'd keep the note documented.
Brute force techniques
Though fairly graceless, one of the easiest ways to recover your music from an iPod is to make the iPod’s music folder visible and then drag it over to your computer’s desktop. Once there, simply add that folder (and the music within) to iTunes by dragging the folder into iTunes’ main window or using the program’s Add to Library command (found in the File menu). Here’s how to do this on either a Mac or a Windows PC.
Macintosh The Mac doesn’t include a utility for making invisible files visible so you must download one. My favorite tool for this job is Marcel Bresink’s free TinkerTool. Once you’ve downloaded TinkerTool, follow these steps:
If the music library on your iPod is not linked to iTunes’ music library (as would be the case when you’re restoring your music library from your iPod to a fresh copy of iTunes installed on a reformatted drive), iTunes will ask if you’d like to sync the contents of the iPod with the contents of the iTunes library. Click Cancel.
You’ll discover that several more items now appear in the iPod window. Among them is a folder called iPod_Control.
Inside the iPod_Control folder you’ll find a variety of folders. The one you care about is the Music folder.
In earlier versions of iTunes you could simply drag this Music folder to iTunes’ main window and the music within it would be copied to iTunes’ music library. This is no longer the case. You must now open the Music folder, open the the folders within (these folders all begin with the letter F), and then drag the contents of the folders into the Library entry in iTunes’ Source list.
The songs you copied from the iPod will be added to iTunes. If you’re a tidy type, before copying those files to iTunes, open iTunes’ preferences, click the Advanced tab, and make sure the Keep iTunes Music Folder Organized and Copy File to iTunes Music Folder When Adding to Library options are enabled. Enabling these options will organize your iTunes library in the way iTunes prefers.
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