Manny: Cont
In your first image, I see that around the chain plate (which looks like it goes thru the caprail) the crack will leak for sure into the boat. Looking at the teak deck - every screw holding the teak in place is a potential area for leaks -- and worse yet - letting water into the structure of the deck... ie on Westsails the deck is a sandwich of fiberglass/plywood/fiberglass. If water gets into the plywood core -- then it will over time begin to rot and the deck will develop soft spots.
In the last image, I see the crack between the laminated caprails - for sure the water can get into this area and begin rotting but also I'm NOT seeing the chain plate on the outside -- so it may extend into the interior of the vessel. All your stainless steel chain plates will need to be checked for cracks caused by oxygen starvation and moisture. If I saw the cracks and pockets of missing filler on a Westsail - I would suspect that bondo was used to fair the bulwarks and now the bondo is beginning to fail.
Link to images of chain plate repair.
Last here is a link to an album with pictures that show "Items that fail" there are quite a few images of chain plates that have failed.
Fair Winds
Jay Bietz