WWP2
I hate to say it but I have never seen such a self bail mess in my life. That setup is a after market screw up and given the right conditions can cause you to sink
Bottom Line, It appears the bottom has been ground down till you now have a hook in the hull. You need to fill those holes up, take off the faring block, re-glass & true the bottom and run some decent floor drains out the transom as I previous suggested.
Some others (Don Herman) need to chine in here.