Hi Joe. Is Denali still moored in Coon Bay? I have seen her a number of times when I have sailed Norwegian Steam over there to visit my friends Mark and Ginny Bell.
Norwegian Steam was hull number 10. I can tell you how her rudder was built and attached. The same construction was used for a number of other hulls built around the same time. The end of the keel, just aft of the "Brewer Bite", is heavily glassed. A bronze foot is fitted to this glass "nub" and is through bolted, port to starboard. The bronze foot contains the bearing, and the rudder shaft rests on this bearing. The rudder shaft is a stainless steel pipe. The rudder itself is fiberglass, but there is a stainless plate inside of the glassed rudder and it is welded to the shaft. The bronze foot is glassed over for some reason (probably appearance).
Because of the weight that the foot must bear, there has always been a bit of a crack in the fiber glass at the level of the top of the bronze foot, on my boat. There has also been some "weeping" from this crack. Years ago, just as you, I became concerned about this. I had Seaview West boatyard look into it. They told me that they did not believe it was a problem and to stop the weeping would be difficult or impossible. The weeping shows, however, that there is salt water in the assemblage and from a corrosion point of view, that could be a concern.
I have a sizeable zinc affixed to the hull just above the propeller shaft. On the outside of the hull, this zinc is attached to a copper plate, and this plate is through-bolted so that a wire can connect the zinc circuit to the engine but also to the rudder shaft. I did this to minimize corrosion, given that the rudder assemblage contains dissimilar metals.
In the case of Denali, You may only have a case of fiberglass fatigue. That could be fixed by removing the foot, repairing the glass at the aft end of the keel and replacing the foot. I would certainly look for corrosion, because previous owners may not have thought of this.
Good luck.
Alan
SV Norwegian Steam