The easiest way to start this process would be to convert the
flying dutchman ghost ship in SH4 to be player controllable. Then create some specialised scenarios with other of the same models and tinker with stats until you have what feels like a realistic damage model for round shot.
I think I'll try and do this in the next few days
Once you have this, then the real work starts.
You'd need to find a way to approximate the effect of wind on maximum speed, and the arc at which you may not sail upwind -
if this is even possible! And if not, one has to ask oneself how necessary it is for the game to still be fun.
You'd need models: lots of models and for that you need people with the patience to learn how to use 3d modelling software like Wings3D
You'd also need to produce a campaign layer
and much much more.
It would be a very large undertaking.
How stubborn are you?
