Somewhere around the daggerboards.

The last three regattas I've sailed the boat at, its taken on a half a cup of water in each hull if that. This level of water ingress is definitely NOT something that was present when I sailed the boat the last couple times.

Since I've had the boat, I haven't grounded it or hit anything with it, so I'm not sure what the problem is.

Mischa did tell me that there was a leak inside the bolt rope slot for the tramp.

As for the tiller arm being cracked - there was play in the arm, but they all have a little play if they aren't epoxy seated, and to be honest, I'm not about gluing those things into the castings. There was nothing visible on the outside to indicate that the arm was cracked.