iDump offers freeware fans a quick and slightly dirty way to copy music from an iPod to a Windows machine. Of course, by "dirty" I mean "unclean," as in, iDump runs a bit unstable.
Regardless, the app shows you the song's iPod path, cracking Apple's unusual file-saving protocol. A main window tab takes you to output options, and from there you just have to choose your songs and hit Copy. Clicking once on a song selects it, and there's also a smart feature that plays the song you've selected in iTunes.
The interface is a clean, spreadsheet-style layout that displays all music on your iPod. That lengthy list can be narrowed via the search function. Songs can be organized by terms as familiar as song name or artist to the more esoteric year, bit rate, or even location on the iPod. Clocking in at under 1MB, iDump is small enough to live on your iPod. I'll let you figure out why that's a good thing.