A wind speed and direction indicator would be great. Really sucks to just stop dead for no reason. Plus most pirate ships never sailed under the Jolly Roger till they attacked, so you shouldn't be getting hammered by everything every time you leave port. Most pirates used someone else's flag to confuse target vessels.
Good concept... few issues I see. The AI never has to clean (no added expense there for the AI), the AI never is rob (no loss of money there)... yet the player gets penalized for both of these things... All in all not a great game.