iPod.iTunes

Within iTunes or the Finder it is not possible to transfer tracks or playlists from your iPod to your Mac(s).
iPod2iTunes (i2i) is the only utility which not just copies tracks but synchronizes tracks and even playlists from your iPod(s) to your Mac(s). The synchronization ensures that you don't produce duplicate MP3 files on your Mac as it is possible if you just copy files from the iPod via other methods.

Track transfer: i2i shows you first which of the iPod tracks are not on your Mac. You can chose some or all of these tracks to transfer them to your Mac:
- based on artist/album.
- based on genre/artist/album.
i2i can transfer the MP3 files seamlessly into your existing MP3 collection and creates folders & subfolders as necessary.

Playlist transfer: i2i can synchronize the iPod playlists to iTunes. This creates the iPod playlists in iTunes with only those tracks which are really on your Mac (you don't get "dead tracks" if you haven't transferred all tracks from the iPod). This feature works also if you have used another method in the past to transfer tracks.

Track transfer history: i2i creates for every session a date&time stamped playlist which shows the tracks which you've transferred to your Mac. This makes it easy to add those tracks to existing playlists or to create new ones from the just transferred tracks.