I recently needed to get some audio files off of an iPod. As many people are aware, Apple has made this non-trivial without 3rd party software. Luckily, iLounge has a rather comprehensive guide to getting content off an iPod, with info for both Mac and Windows users. Wikipedia has an even more exhaustive comparison of iPod managers, for those that need it.
I ended up using the free Senuti 0.33. It worked quickly, and since I mostly wanted to look at the metadata it was fine. In the comments on the iLounge article, people mentioned iPodDisk as another slick alternative. The 2.0 beta uses MacFUSE to allow one to directly browse the music on the iPod with metadata. I only needed to do this once, so I didn’t try iPodDisk.