Was the water dripping from the anchor locker to that point and then to the ballast cavity? Can water that ends up in the space below the sole make it to the real bilge aft of there or does it pool up and hang out? This is the first time I've seen that space, thanks for posting that photo.

BTW- I removed the rudder shoe tonight and it is in great shape. There was a small amount of water dripping out of the holes the pins were in though. I'm going to let the area dry for a while then overdrill the holes, fill with epoxy. Redrill the correct sized holes then rebed with an obnoxioius amount of 5200. Fun Fun!