This is my next project. As you can see trying to make this waterproof would be a nightmare at best so I am planning on moving the mechanical part above the deck using the old rudder bracket which is still in place.

This is the rudder refurbished and back in place. My rudder shaft is solid stainless so the original method of lowering and raising it will not work. Instead I will use a pole with a hook and a small hole in the lower part of the rudder to do the same job.

As seen here I have moved the rudder mechanism above deck into a small housing made out of 2X redwood. I had to modify the shaft which was made for a tiller to fit in the wheel housing.
This is the final look, I will probably have to turn the wheel around to clear the main sheet rigging but I won't know for sure until I stand the mast. The notch in the wheel will be up normally to allow the mast to pass through to it's support during transport and erection.