thank you miranda and LAB for your help.
Besides the 2 sites you have mentioned, I've found a few more.
http://shuffle-db.sourceforge.net/http://www.yamipod.com/main/modules/home/http://www.mlipod.com/ (winamp plugin, so I probably not going to try it)
I actually bought the Nano as a gift for a relative of mine and I'm just trying to find the easiest way to u/l songs with additional software.
I guess I will test out all the options and see which is the best.
Thanks again