Re: cedar shakes cupping
I'm gonna guess it's partly due to the fact that the undersides of the shakes are not painted, therefore in wind-driven rains they get wet while the outside sealed for now with some superpaint remain dry. This could be avoided by ordering the shingles pre-dipped in stain, and could have been made less troublesome by laying them over a mesh rainscreen product. At this point there's nothing to be done but get used to the post-deluge warping.
Remove not the ancient landmark, which your fathers have set.