Chuck,
As you are aware, I'm new to all of this, so please forgive any naievity in my questions. I understand that there is some water in that area, that make sense to me. All boats leak, you're going to see water around the chainplates. How far away, how much, etc., is another story, but I find it hard to believe that any boat will be perfectly dry, especially around an area like that that is subject to dynamic loads. The deck penetration is a weird shape and it's got to be tough to keep that properly sealed (not that you shouldn't try!).
But what I don't get is how the surveyor connects the moisture at the deck to the problem you showed in the picture. If it was winter, I could understand that water got into the area, froze, and then created the cracks you saw. Obviously, that's not the case. Is the surveyor saying that the water also penetrated deep enough that it weakened the chainplate/hull joint so that the forces were concentrated on a small portion of the chainplate? If so, is that cracking near the bottom of the chainplate?
Sorry, I don't mean to dwell on this, just trying to learn.