Let me introduce you with a straightforward way for Windows users to transfer music from an iPod to your hard drive, without extra software:

1. 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.
2. In Control Panel, Portable Media Devices, double-click your iPod.



3. Navigate to the Music folder.
4. 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.”)

If you give this a go, lemme know how it goes. I’ll amend the instructions with any additional info for other versions of Windows and iPods.