iTunes can certainly present a challenge when syncing content to your iPod but can be unforgiving if you need to get content off an iPod which has not been associated with a given computer. Most people would give up thinking their music is unable to be retrieved and proceed to wipe their iPod and start again.
However, this can be rather problematic if you’ve lost all of your music on your computer though and the only copy that remains is stuck inside your iPod.
As luck might have it, there is a fantastic piece of software called SharePod that will retrieve your content from an iPod and even sort it into folders by artist and album if you so wish. Apparently, SharePod requires iTunes installed to work but on my Windows 8 ultrabook which has never had iTunes installed it worked just fine when extracting music for a colleague whose iPod had gone on the fritz. You may have to be a little patient though, it took five to ten minutes to extract about 1200 songs from an iPod nano (about 5GB in total).