Great AAR and beautiful setup.

For question no 2: With 2 leak damages and 1 crew action left, your ship should be doomed.

The repair action blocks the crew action for two turns.

a) 2 leaks
b) 2 leak damage tokens - planing repair
c) 2 leak damage tokens - repair
d) 1 leak damage token - planing repair
e) 1 leak damage token - repair

If your ship can suffer 6 boxes of incoming water with only 1 crew action left...

Maybe after a grape shot stern raking shot from HMS Victory...