That might be possible to implement, actually. Just like how clicking on facebook spotify 'listen with' links now plays the song in the _spotify_ app, there may be a way on the server to control what the client does...
However the File object hides the full path from the JavaScript code for security reasons (see https://developer.mozilla.org/en/DOM/File). I assume most dropped files would contain the user's home directory and therefore account name in the path.