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Well I made it back out to the boat this afternoon, seas were calmer so I was able to go down back and bail (had a 5 gal bucket on board but it got washed over the transom when the stern took on water). Turns out the bilge pump battery wasn't dead after all, the wire going into the in-line fuse holder corroded and disconnected... Timing. There was some seaweed etc in the sump, but the pick up screen was clean for the most part.

Both the batt boxes and oil tank box had significant water in them, so the stern must have taken some good water over it while the boat was flooded. Didn't appear to be any water in the oil, but I'm going to tip on a corner and siphon some out from the bottom anyway.

Both the anchor locker in the front and the large locker just behind it had some water, but not as much as I've had in the past from rain, and it was very cold (meaning it was rain water and not sea water) so I don't think it was taking waves over the bow. I think this was all stern induced and moving the batt's and oil tank fwd should hopefully help.

The pennant that attaches it to the mooring ball is standard length of at least 2.5 times the height to the bitt, so I'm not sure if that was an issue or not. I'm wondering if the canvas on the T-top acted like a kind of sail when the bow would go up on a wave, pushing the stern down into the water more than it should?

But all that being said, she still behaved like a Whaler when I pulled the rear drain plug in desperation. Didn't self bail nearly as much as Jeff's previous Outrage, but it was enough to get the transom above water and drain the deck. Can't beat that!