This has worked for me in the past.
http://lifehacker.com/105256/how-to-copy-songs-from-your-ipod-to-your-pc
How to copy songs from your iPod to your PC
By Gina Trapani, 1:20 PM on Fri May 27 2005, 803,220 views
Update, May 2008: For newer iPod models, see our complete guide to copying music from your iPod to your computer.
A reader points out a straightforward way for Windows users to transfer music from an iPod to your hard drive, without extra software:
Connect the iPod to your PC. If iTunes starts syncing (ie erasing) your music automatically, hit the X in the upper right hand corner of iTunes display, to the left of the search box, to stop it.
In Control Panel, Portable Media Devices, double-click your iPod.
In the Tools menu -> Options, in the View Tab, check "Show hidden files and folders."
Navigate to the Music folder. On my 2nd gen 'pod, the full path is Portable Media Devices\GINA'S IPOD (F:)\iPod_Control\Music
Select all the music folders, and drag and drop them into a folder on your hard drive, or directly into iTunes.
And you're done! The iPod music folder structure is strange and inexplicable, but once you move your files into iTunes you can set it to automatically organize your folder by artist and album to clean that up. (To do this, in iTunes Edit menu, choose Preferences and in the Advanced tab, check "Keep iTunes Music Folder organized.")
This is great information. There is a catch though. I think as long as the data (songs) came from the same PC you're ripping them back onto, you are probably okay.
I've picked up shareware ripping software a couple years ago and copied "other" iPods to my PC. Depending on the way the songs were purchased, i.e. you owned the CD's you put into iTunes and then your iPod, or you purchased them from iTunes' iStore, you may not be authorized to play them.
I have lots of songs on my system that are there, but unable to play because of one reason or another.
I know have just over 12,800 songs on my iPod and that isn't all that's in my iTunes. I have lots of classical that I can play, but just not on the iPod taking up space. I have not purchased many CD's in the past 5 or 6 years, but still I have over 800 CD's in my collection. With the songs in iTunes already, I still have over half of my CD's to download into iTunes.
What I've started to do lately, is rip the audio tracks from DVD's. Sometimes a concert is only available on DVD and you really like the way they did it in the concert rather than some other CD. I have ripped both of the Eric Clapton Crossroads concerts, TX and IL. Some of the artists did things on stage that is not available anywhere else.
Just food for thought.