Ward Peyronnin: "So I struggle to rate these courses right now and I have at least 3 I am circling around weighing what exactly constitutes playability and how much weight does playability carry in my assessment?"
Doesn't this go to the heart, and fallacy, of the rating process? Are you rating for the highly skilled golfer, and if so, for what skills? Or for the average recreational player? Personally, I pay no attention to ratings of the kind you are speaking of (I think), but my wish would be to see ratings based on playability of the courses for the average recreational player. Maybe separate special ratings for the most penal, difficult courses.
Your handbook says: “Greens and surrounds- Interest, variety, and playability of putting surface, collars, chipping areas, and greenside bunkers.”
Forget the near impossible designs. What does your "cranky old self" want today? I'd guess that might be what is fun for you and would also be for the vast majority of other players. It seems to me that your gut is telling you to go one way, but that's against what you see as a trend. Go with your gut. Just my opinion. As cranky and old. Others may disagree, but I find that the older I get the better my judgment gets.