Probably not the right thread for this, but here you go. If you start with your own flag raised, you can get out of Oxbay just fine. Generally speaking, putting surrendered people to the sword, or feeding them to the sharks, are not the actions of an honorable person. Ergo the reputation hit. To fix up your fast schooner, go to Quebradas Costillas and have the Pirate Shipyard patch it up for you. As for your reputation, if it concerns you, start doing "good deeds". Talk to everyone you encounter in the towns and warn them of their purses falling out. Get your money back from pickpockets but don't accept the stolen gems. Give donations to poor folks that ask you for money. Rescue wayward damsels in distress in the jungles at night. Or, my personal favorite, sink every French, Spanish, Dutch and Pirate ship you come across and rescue the men overboard. Prior to doing this last, I recommend getting a Letter of Marque from Silehard, the governor at Redmond. Your experience level, rank and personal wealth will go up very quickly this way. Of course, the downside to this is your crew money will not go up as quickly as you won't have all those ships to sell, but everything in life is a compromise. There are portions of the main quest that require you to have a reasonably decent reputation.