Re: question about older ketch or yawl handling
There is a lot that can go wrong, a simple but sensible scenario is the need to keep sail up for speed, in a situation with rising wind. As the wind increases the boat will get harder to control because she is overpressed and eventually she will broach. The answer is to reef, or take in sail, but you can write it any way you want. They can reef early, or they can try to keep the boat going fast when she is overpressed, or they can broach and then reef.
You have a lot of options for trade off scenarios, where they can go for control or speed. You can also have one boat try to out point the other, and what works in lighter winds may not work in heavier air.
You can do the reverse, start with high winds and less sail up, but have the wind die and the crew need to keep adding sail. A ketch would have a nice set to work with, and its hard to fly a spinnaker on a big yacht with only two crew.
Yachting, the only sport where you get to be a mechanic, electrician, plumber and carpenter