On the good news front, the boat is already on the hard so that is not an issue. After looking at everything I am feeling like a full replacement of the hose (and shortening it) and stuffing box is the right move. That, I'm sure is full of challenges, one of which is the rudder drop (which I was thinking about doing anyway for preventive maintenance). Am I reading right that this cannot be done without digging a hole to make room for the drop? I am really interested in doing this myself. Despite what I'm sure will be a TON of frustration, I really do like the learning experience of it (as long as I don't sink the boat).