But it does, doesn't it? By the width of the hull?

Because there would be only small frictional losses as the rope runs over the hull most of your downward force would be at the boats maximum width. I would also suggest that you have moved your rotational force closer to its apex.
What I'm trying to say is that when you go Hawaiian your attachment point has to rise further off the water in order for the mast to come to horizontal. This is while you are pulling down on it. With over-the-hull I imagine it as describing a more lateral movement as the hull works as a pulley.