If you do this through itunes, it should be okay. The trouble is everytime you want to update your ipod, you will need to connect it with itunes and itunes will need to have your existing library that you created for you ipod to perform a quick and troublefree update.
If you are going to get an external harddrive you will need to re-direct where itunes is saving your music and video files. Because itunes will be using your internal harddrive for the system files (that is where windows is), it will automatically save the music to your internal drive. I suggest reloding an updated version of itunes from
http://www.apple.com/itunes/ here and when asked where to install it, redirect it from C:programfiles.......to your external harddrive. This way the itunes music folder will be on your external harddrive.
Hope this helps
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