Clark... while you are talking abou eyes, I have noticed in some visible satellite images of intense hurricanes, the indentation around the eyewall (the "calm" I guess) only going down to a certain depth (ie you wouldn't be able to see the ocean while flying around in the eyewall). Something similar happened with Isabel a few years ago:
EDIT: While you wouldn't need a cat VI rating (as you said, the damage is allready complete at category 5) you could probably technically do it for those "once in a quarter of a century" storms like Gilbert, Mitch, Camille, etc.