I removed and re-installed the rudder on Midnight Sun when I was a LOT younger. I remember having to weigh it down with two anchors, chain, and a divers weight belt. Even with that I had to stand inverted underwater with my feet on the hull. Even with all that I think it was easier than digging a hole for the rudder to be dropped into while the boat is on the hard. The only other way is to find a very friendly yard that won't mind hanging your boat in the travel lift for an afternoon. When my rudder was replaced a couple of years ago after the container incident, The yard did just that. It was still disconcerting to see the boat that high in the air. Ed, I don't have a pin in my rudder stock, just a piece of flat plate welded vertically that fit the notch in the emergency tiller.