OK, didnt read this all, sorry, so just tell me to shut up with dumb ideas.
when rings of different sizes meet I think what you really want to do is NOT calculate a ring of polys, you want to calculate a ring of vertices, and then connect them to the previous ring. That will give you sloping surfaces. Store each ring of vertices in an array and use the last and current arrays. the patter of vertices assigned to each poly will be the same for each ring given the same number of segments in the ring.

its good anyway, can always touch it up in a modeller. Attack of the mutant spiders is now possible :)