How To: Download Music from the iPod
Getting music off from an iPod is not a thing most of us worry about until the inevitable happens - a desktop PC crash. Imagine over 25 GB of music stuck in your iPod and a empty playlist in the PC. If you haven't yet experienced it, you cannot Sync iTunes and get all music back; iTunes will not sync back the music from the iPod to a crashed PC. Thankfully, there is hope - in two versions; iLinkPod for the Mac and EphPod for Windows.
From the iLinkPod site:
"iLinkPod is first of all a unique tool that creates a permanent and direct access from your Desktop (and your iPod or wherever you want) to the hidden folders in which iPod stores your audio files. All this in the safest way, without modifying any file/folder or configuration file of the iPod! Direct access means that you'll access your previously hidden audio files directly fromthe Finder, while they remain hidden! (remember: iLinkPod will not modify any properties of files on your iPod!). So you don't need iLinkPod or any other utility to access your hidden audio files on the iPod, you'll have access to them through a common folder on your Desktop (and iPod too). You don't need do execute iLinkPod again if you add or delete/modify songs on your iPod, you'll have access to your iPod as it is in that moment!"
Simply put, iLinkPod creates a link to all the hidden music on your iPod so that you can drag and drop the music files back to the Mac. iLinkPod is free for download and claims to work with pretty much all iPods.
EphPod is the Windows version of the life-saver. EphPod can export music from an iPod but also do a number of additional features like importing Microsoft Outlook contacts, latest news, weather, e-books and movie listings to an iPod. EphPod is also free like iLinkPod.
Of course, as you do realise none of these utilities are supposed to be used for "stealing" music. And you use them at your own risk.