No Problem
Yes, you can tighten the rudder post nuts while in the water. Those nuts do not hold the rudder up. There is a collar around the rudder post higher up that holds it. There is also the wheel holding the steering cables.As I mentioned in the photo forum, those nuts may be frozen in place on your 20 year old boat. Give them a good soaking with stuff from your local automotive parts store. Let sit for a while, then turn the bottom nut clockwise. This is the locking nut, and may take a few taps from a small hammer and chisel, or a couple wrenches. This is a very tight area to work in, so long handles are out. I used a large pair of channel-lock pliers.Once the bottom nut has turned a turn or so, turn the larger top nut clockwise and snug it up. This compresses the stuffing material, and should stop the leak. Tighten the locking nut when finished, and check it after a day or so. If you can't get the leak to stop, you may end up replacing the flax. I would hold off doing that until the boat is pulled out of the water. Your bilge pump should be able to handle so leakage from the rudder stuffing box.Ken Palmer, S/V Liberty