At the time that I had the problem I had no idea of the solution and expected a big boat buck solution would be needed. Fortunately my fav yard guy, and this is a marina that is 99% power boats, recognized that it should just be the caulk. He very easily recaulked and the moisture disappeared. The boat was in storage at the time.
I am quite sure that he did not need to drop the rudder at all. Just got the old caulk out and replaced.
Fred Rachwitz
Concerto
NS 30U #445
Harbor Springs, Michigan
Northern Lake Michigan