The rudder is hollow as I'm sure you know. If you over tighten them you can crush the rudder. One of the boats that hauled at Ladd's for the Dave King mods had the bolts tightened so much it was crushing the rudder and was subsequently repaired. We added 3/8" graphite tubing as compressions posts to prevent this and allows the bolts to be tightened without crushing.
Jim
Life Caulk is probably a better choice but we used 5200.