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While redoing my Catalina 27 this winter, I rewired the entire boat including the mast. After trying to find an acceptable (to me) method of getting the mast wiring into the boat, I decided to try the method that I have seen a few times on this board. Here are two pictures, one from inside, one from outside. This works great, has been totally leak free and makes it easy to add wiring later if needed. Thanks to everyone that had shown a version of this method!
It is indeed a 45 degree pulpit base. I originally decided to use the fitting because it let me get away with a smaller hole since I didn't have to fit that honkin piece of hose inside the mast. After is was done though, I think the aesthetics are as much of a bonus as the smaller hole!