There is, however, one flaw with this method. If you have iTunes sharing enabled, your iPod's contents wont show up. The solution? Turn off "Copy files to iTunes Music folder when adding to library" under Advanced preferences, then add the music files on the iPod to your library directly. The way things are set up in iTunes makes this somewhat tedious, so I wrote an AppleScript to do it.
robg writes: Due to the length of the script, I've uploaded it as a text file; click here to view the source in a new window, and then copy/paste into Script Editor.
A couple caveats:
- Rather than adding each file to iTunes as it finds it, the script makes a list of all files to add then adds them all at once. It runs much faster this way, but it means that during the first portion of the script, there will be no feedback. Be paitient, and eventually, iTunes will give a progress bar during the add phase.
- If you want files that end in something other than ".mp3", ".m4a" or ".m4p" to be added, you'll need to add the appropriate suffixes to the extensionList property at the beginning of the script, or just wait for the script to prompt you for every file with an unlisted extension.
- The file names on the iPod don't include all unicode characters, so for best results, make sure the files have ID3 tags.
- Information which is stored in iTunes private database like My Rating and Play Count will not show up in the library, but will be maintained on the iPod.
- I tried to write the script to intelligently handle the case of multiple iPods, but as I don't have multiple iPods, I couldn't really test it very well.

