Re: Cockpit drain question
As Faster said flaps solve the water in problem.
Many cockpit drains are crossed under the cockpit as when heeled the lee one may be below water level otherwise, and they work well.
If it drains slowly an additional one may be installed in the transom, but I would keep the 2 originals.
I believe the op is in San Francisco and it is not in the hurricane belt.
Living aboard in Victoria Harbour