You shouldn't have to unplug/re-plug the drive to transfer your files. That is an inconvenience that you don't need to live with. It's probably best to get the Touch's built-in file sharing (Samba) sorted out, but even if you don't manage that, you can probably use WinSCP to transfer any music files. You only need to navigate to the music library via WinSCP, as opposed to navigating to the location of the server.prefs file.
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