Tradewinds

Bounty Hunting:
Once you have gotten a sizeable fleet, you can start hunting notorious
pirates for bounties. Each bounty isn't worth all too much, but it seems
to be greatly multiplied when you collect multiple bounties all at once.
4-5 bounties can be upwards of 150,000 gold, where as each bounty
individually might be worth 10,000. 7 bounties can be up to 1,000,000,
9 bounties up to almost 2,000,000.

Hints:
The first and most important tip is to avoid naval combat at all costs
early in the game. Every time you destroy a pirate ship at sea, you’ll
add more ships to the pirate fleet, meaning that the next encounter will
be against at least one more ship. Wounding a pirate ship doesn’t count
as destroying it, but it’s generally better to run anyway. When you’ve
built a fortune, you can sail around with twenty five heavily armed ships
blasting away to your heart’s content.

Midway through the game, you’ll need to earn large sums of money to get
to get further along in your career. Pay attention to the inn, and pay
for people’s drinks. You’ll 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 you leave the game and come
back to it (that includes saving and loading your game), but they stay the
same as long as you keep playing, so use that to your advantage.

Once you’ve accumulated a large fortune, you won’t want to haul cargo
around to your various ports to make money. Instead, purchase the warehouses
in each port, hire guards, and then start buying bulk amounts of the products
you’ll be selling. By tracking the tips from the inn, you’ll be able to
stockpile the precious resources in each port, selling them only when a really
good deal comes along. This is far quicker than transporting cargo by ship,
saves you tremendous space; you can use that space to arm your fleet with more
cannon , keeping it safer. Plus, the tougher your fleet, the easier it’ll be
to take on the pirate captains that offer small bounties and big status rewards.


Your information on Bounty Hunting is incorrect:
Submitted by: Cat

The bounty does not scale with how many bounties you have. Speaking with the bartender,
you learn that the port authority sells 25 crates of silk to pay the bounty. So unless
you are short on cash, you want to save them until the price of Silk at the port you
are in is high. (Highest price seen is 2600gold. This equals up to 65,000 per bounty.)

Asking the Port Authority for news will tell you between which ports the wanted
captains are going.

Once you have a fleet strong enough to take on the pirate fleets, start plying your
way between them for big money. (You get the bounty plus whatever you get from
defeating the fleet.)

If you are not in a port that leads to a captain, (for example, the current pirate
captain is between Jia-Ching and Tanchon, but you're currently in Lama Sut) it is a
prime opportunity to load up on Dream Dust (if it's cheap) and stop by Shangri La
to sell it.

Shangri La has no Port Authority, so there is no fear of having this contraband
cargo confiscated, and you can easily double your investment.