No, it’s not hard, but not being able to transfer music back off an iPod was the price Apple had to pay for setting up iTunes, otherwise the recording industry would not have played ball.
There is software available that allows you to copy back from an iPod, some free, but with limitations, or paid for, which is more versatile. It’s something I had to do once, after managing to lose 80Gb of music from my laptop, which was distressing.
What bitrate is your music ripped at on the Pod?
Reason I ask is that if it’s all at 256kb, you could connect the Pod to iTunes, and upload it into iCloud, then download it back onto your computer.
Meanwhile, I’ll see if I can find out what I used to copy back with, my PpowerBook is out of commission at the mo’, and I don’t think I have it on my Mini.
Right, here you go:
http://www.theboysdownunder.com/ipod2itunes/