When the hard drive containing all of my iTunes Music Store purchases failed, I was mildly annoyed, but I assumed Apple would let me download my purchases again. Unfortunately, that's not the case.
Luckily, I still had the music on my iPod. But iTunes doesn't let you copy music from an iPod to your hard drive. :(
So I wrote a program to do so! And you can use it for free. So if you've lost your iTunes music, and want to retrieve it from your iPod, give this program a shot.
This software is provided with no warranty, and may not work as expected. Let me know if that's the case.