My first impression is that the cockpit would not drain with the drains crossed. When the boat is healing the exit point of the drain line on the topsides would probably be above the cockpit drain level and water is not fond of running up hill. There is very little (at least on my commander) distance from the cockpit floor to the waterline level. So even a modest heal would cause the water to stay in the cockpit.

Am I understanding the plan correctly or am I all wet??????????