For iPod to computer, iPod to iTunes transfer, I recommend this iBackup-iPod transfer software
It was designed to help copy all music, videos, photos, playlists, podcasts and more from your iPod to your computer and iTunes in the quickest and easiest way. And with it, we don't need to worry about any data loss. Then you can sync smoothly.

Just free download it to try. It works like a charm. It will save you lots of time on this.