basically it sounds like you just have to point each app/software to the same music folder, then do your uploads seperately to each through their own software.
with that said, read these on phatnoise:
http://www.phatnoise.com/kb/index.ph...v2&id=132&c=12
http://www.phatnoise.com/kb/index.ph...v2&id=507&c=14
http://www.phatnoise.com/kb/index.ph..._v2&id=120&c=9
also, you wont get that much onto your nano as it is only 2GB or 4GB
another thing, this is why I do not like the iPod/iTunes combo and its DRM.