If some of your bazillion songs on your ipod were not purchased using itunes (for instance, ripping a cd, or perhaps downloading from a torrent site), using a transfer program won’t work. The new itunes library on the new laptop will not recognize those songs and you’ll have to transfer them in other ways. Trust me - we had to do this over Christmas with my daughter’s ipod.
Google using your ipod as a hard drive to transfer music. Print the instructions and go from there. It was easy.
I have never purchased a song from iTunes. My iPod consists entirely of mine and my wifes CD collection. Which, having worked at a radio station many years ago, is freaking huge.