I was out at Bruce's on Tuesday for a second game of Fighting Sail (an Osprey set). I recall quite liking the rules the first time we played. The mechanics are very slick with variable movement, easy combat and simple damage tracking.
Things started out okay, with both fleets running with the wind towards contact.
Then things got really good as my rolls turned hot and one of Bruce's ships took a real pounding. We had a coupe of ships disintegrate after a combination of close-range rakes and hot dice. I wonder if the ships were a bit brittle? But so far so good.
Then we ran into a real mechanical problem. The ability of the ships to fall with the wind means that when the game gets into a knife fight, whichever player rolls lower on initiative (and goes second) has a huge advantage. We had turn after turn of rakes as the "loser" in the initiative roll swung into the best position. While the initiative winner fires first, if you are getting raked, you don't have much of a target!
This seems to be a design error (as one of the "advantages" you can have is a great admiral who can increase your initiative roll--pretty much the last thing you want). We couldn't figure out an easy fix (which was too bad as the rest of the mechanics are awesome. Maybe simultaneous orders? But that is hard to incorporate give the variable move distances each ship gets each turn.
I had fun and all but this seems like a pretty major (and obvious) issue with the rules (unless we were playing them incorrectly--but I don't think that was the case).