Hi,
You got the right person.

I always transfer my iPod songs to my PC to backup iPod files.

I have been using an iPod to iPod/Computer/iTunes Transfer and it always works well.

You can download it free here:
http://www.bestdvdripper.biz/ipod-files-transfer-avc.html

It can transfer your iPod files including iPod Photos/songs/videos to your computer to backup your iPod files.

Just try it and maybe it can help you.

You may take a look at this step by step guide, it will teach you how to copy all music and video from iPod back to computer or iTunes, including the non-purchased music (such as CD music, downloaded songs), it's safe and works pretty well for me.
http://www.ipod-transfer-copy.com/how-to-transfer-music-from-ipod-to-computer-itunes.html
Hope it helps. Feel free to email me if you need further help or use http://www.answer.com to search more answers.