One of the biggest problems with the iPod is that officially you can't get your songs off it (amazing ah?).
There are a few ways to get around this limitation but one of the easiest is iDump.
Forget this program's awful name (actually it's pretty cool :).
It allows you to easily transfer your songs off your iPod to a PC.
All you do is connect your iPod and run iDump and you'll have access to all your songs and even your playlists.
Just select the songs you want to transfer (you can even use your playlists to select songs) then pick a destination directory and how you would like your songs to be named. And then sit back and transfer all the selected songs to the PC.
Dump away...