Al,
You are right that the rigging is a pain. Your boat has relatively new cheek rubbers to help hold the rudder in the full down position, but in rough weather it would still creep up. Even 1 inch of creep (at the rudder tip) is enough to cause severe steering strain. I used to not only tighten the wing nut, but also tighten the pivot nut down more snuggly with a wrench to help hold the rudder in position. Of course, then you have to loosen both the pivot and the wing nut to raise the rudder.
A friend of mine screwed in a small pad eye near the tip of the rudder and looped his uphaul down through it which gave much better leverage to raise. Using a thinner high tech line would keep the drag down if you do this.
I used to raise the rudder part way with the uphaul, then hook near the tip with the boathook to fully raise. However you do it, its an adventure, but worthwhile to tuck into those peaceful shallow gunkholes.