I don't have an Ipod but I have watched my son who also has an Ipod Nano. I once managed to wipe all his stuff off the thing, and to this day don't know how. All I know is that next time he connected it to the pc it synchronised itself with the library on the pc and restored everything to the Ipod. I also heard him berating his brother for starting Itunes from his desktop while the Ipod was recharging, and it replaced everything on his Ipod with everything in younger brother's mp3 library. Thus I have formed the impression that the library on the pc is the determining factor rather than what's on the Ipod, hence my suggestion. The expression 'am I missing something?' is a lazy way of asking is the question more complicated than I think it is. It wasn't meant to be sarcastic or condescending, and I'm rather upset that you took it that way.
I think it is always advisable to check the radio button on the ipod options is not set to "Automatically update songs and playlists." I prefer to manually update by checking the manual update button. Hope this helps.
You have the option to launch itunes when you need it and therefore it won't launch as soon as you connect your ipod. When your pod is connected you will see in the bottom right corner an icon that if you click on will open a menu for ipod options. All settings can then be changed from default to your own personal preferences. Just regard the pod as another removeable storage media.
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