-Start in 1635 and travel from port to port. Recruit 100 marines while sailing southwest, then go to the Cayman Islands and attack. Put all marines in the last option area once on land. Take prisoners but not back to the ship. Keep taking prisoners and decline the terms. The town will surrender and you will get an option to sell the prisoners. Click it, then click "Cancel". The money you are rewarded for defeating them will increase each time you offer to sell them and cancel. Note: The more houses you raid, the more the multiplier. Also, raid the treasury but not the Governor's mansion. Having 100 muskets will speed things up.
-Before disbursing your plunder to end an adventure, go out for a final strike on the open seas to kill off some crewmen and get some extra gold. This will make your split much more attractive once you reach port.
-When a ship surrenders, secure it and take it to port to sell. Do not press the crew into service or they will mutiny at the most inconvenient time.