Dear Richard,
My hill #52 1977 came with a grease fitting but I don't know who put it there, could be factory or not. The rudder tube and the associated fiberglass used to install the tube and reenforce the installation look to be about 1/2" thick. Assuming that the grease you use will be lighter than water, it will float on the water that is always in the tube. The tube is open at the lowerend about at static water line, and water can easily seek a level higher in the tube as waves pass the hull or the stern is depressed by motoring. So if the grease is is going to be in there emulsified with water I don't think it is critical where the fitting is placed so I think make it higher than lower, but do it where you can get tools in to do the job. If I were doing it I would drill a small diameter hole right too the rudder post, 1/8" or so then follow up with a larger drill for just the thread depth of the fitting.
Sam
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