Bounties
When speaking with the bartender, you will learn that the port authority sells 25 crates of silk to pay the bounty. Unless you are short on cash, do not turn in bounties until the price of silk at the port you are at is high. Note: The highest silk can reach is 4,800 gold.
Once you have gotten a sizeable fleet, you can start hunting notorious pirates for bounties. Each bounty is not worth all too much by itself, but it seems to be greatly multiplied when you turn in multiple bounties all at once.
Ask the Port Authority for news. You will learn which ports the wanted captains are going between. Once you have a fleet strong enough to take on the pirate fleets, start plying your way between them for big money. You will get the bounty plus whatever you get from defeating the fleet.
Defeating pirates
Start with the character that has the biggest vessel so that when you encounter pirates it will be easy to collect bounties. Do not worry about trading to afford new vessels and cannons. Bounty hunting will get you the funds needed. Make sure you have a fortified navy every time you face a pirate fleet.
Easier start
Avoid naval combat at all costs when first starting. Every time you destroy a pirate ship at sea, you will add more ships to the pirate fleet, meaning that the next encounter will be against at least one more ship. Wounding a pirate ship does not count as destroying it, but it is generally better to run anyway. After you have built a fortune, you can sail around with twenty five heavily armed ships blasting away the pirates.
Easy money
Midway through the game, you will need to earn large sums of money to progress further in your career. Pay attention to the inn, and pay for people's drinks. You will hear tips that will help you make financially good decisions, such as buying cheap dream dust, or selling arms at a high price. These tips change randomly each time the game is restarted, (includes saving and reloading), but they will stay the same as long as you keep playing.
Once you have accumulated a large fortune, do not haul cargo around to your various ports to make money. Instead, purchase the warehouses in each port, hire guards, then start buying bulk amounts of the products you will be selling. By tracking the tips from the inn, you will be able to stockpile the precious resources in each port, selling them only when a very good deal appears. This is far quicker than transporting cargo by ship, and saves you a tremendous amount of space. You can use that space to arm your fleet with more cannon and keep it safer. The tougher your fleet, the easier it will be to take on the pirate captains that offer small bounties and big status rewards.
If you are not in a port that leads to a pirate captain (for example, if the current pirate captain is between Jia-Ching and Tanchon, but you are currently in Lama Sut), use the opportunity to load up on Dream Dust (if it is cheap) and stop by Shangri La to sell it. Shangri La has no Port Authority, so there is no fear of having the contraband cargo confiscated, and you can easily double your investment.
