For this challenge, I made my fleet American, all from the Pirates of the Revolution expansion.
The Enterprise is my flag ship, with 5 2 pt short range cannons, which Crenshaw allows to fire from long range. This means she can hit both "cannot be shot within S" and "cannot be hit by long range cannons" ships. Her built in extra action ability functions within the challenge restrictions since it comes from the ship and not crew, and Jonathen Haraden provides captain and reroll for that extra action. This gives the Enterprise the highest probability for the longest striking distance in the challenge at S+S+S+S+L better than half the time. Several Barbary ships with Jack Hawkins on board can possibly have a greater striking distance, but with no reroller available on any of the good vessels, the chance is only 33%. Being able to fire from L also increases the Enterprise's chances of striking first, since it won't have to worry about cancellers from that range.
I added in the shipwright to the Enterprise since I had the points, and I've found a shipwright on an extra action ship is actually useful - move away from the firefight while the support ship fights, repair, then come back next turn to finish off the battle(or keep running and repairing until you're ready to fight again). The oarsman with the extra action is also useful for running away when mastless. Both tactics work better with a Helmsman involved, but that wasn't an option this time.
I thought about using a ship that had crew eliminating ability like the Louisiana, but then I thought, the best way to eliminate crew is to sink the ship! The Franklin does this great! It may be the best support ship ever. 4 1-pt. equivalent cannons against all factions with S+S speed means she'll be arriving alongside the Enterprise either the same turn or the next (if the Enterprise moved twice with its extra action), to mop up anything remaining from the Enterprise's initial assault.
I included Foul Winds for raking those 6 and 10 masters across the nearest reef to chop them down to size, although with a good chance of the Enterprise firing 10 2-pt. cannons along with the Franklin's 4 1-pointers, I might not need Foul Winds to help take out a 10-master after all. 
Another use for Foul Winds could be to bring the opponent into range for that all important first strike.
Miniature Trading
