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Right click the navigation skill, in the character window, to see what are the skills required for every ship class. For example if you have a sloop that is a class 5 ship, then you (or you navigator) must have at least 25 navigation skill. If not, you will get a lot of penalties (you can see those red numbers with minus next to your skills) and a huge upkeep for the ship.
For money in the beginning it is difficult, you need good officers, a good cannoneer so your cannons be more precise, and do more damage and a doctor, so your crew will not die as easy.
Buy Ebony and Mahogany in Beliz and Blueweld
Sell the goods in Capsterville or Willemstad
I started in St Pierre with a small boat and finished with 2 caravelles and a galleon
Gamers:
Play with governors (as soon as you've reached a certain level 4 or 5). He will play with you.
You can beat him once a day. Save before going in governors'mansion and play dices for 500 pesos at the beginning and after 2000 pesos per dice.
Also during the Dutch Saga, I had two Hot Raids, one heavy galleon filled with 900 gold ingots, split in half with my partner and one trading convoy with vanilla, i got 2/3 of that since I had 2 ships, over 1500 vanilla if i remember right. Since in the later stage of Dutch gambit I could not store any ship, I carried the heavy galleon with gold in my convoy waiting for the price of commodities to rise again.
You should invest a point in the ship skill Raise Dutch Flag. Also,you can pay that priest in Martinique some doubloons to settle the things with Spain. Actually I don't know if he deals with hostile too, hostile is not that bad, but if you fight some more the Spaniards, they will put a ransom on you and that's bad, you will be chased by bounty hunters.
So, you need the Dutch flag, buy a trading license from the Dutch company in Curacao and you can trade with Spain. Spain and Holland are trading, they are not at war. Take care though, the Dutch and English are at war, so if you have the Dutch flag raised, Spain will leave you alone, but the English will attack.
PS you can ask in the store for news and most of the times, the seller will inform you of prices in a a certain city. Also you can send longboats to other ships, talk with the captain and ask him the prices in the city he is coming from. Then, pressing F2, you can get to the trading page and see the prices in those cities. The fact is the capitals like Willemstad, Capsterville and Port Royal buy colonial goods to export them to Europe, so you can buy from the cities that produce colonial goods and sell them in the capitals that have high demand of those goods.
For now, all you can do is fight the small pirate vessels, explore the jungle in every city, transport goods for the merchant, escort merchants, etc. Sometimes there is a guy selling a treasure map in the tavern, so that is a good way to make money. Only once I encountered a fake map, but my character has a good luck skill. This will develop your character and you'll earn enough money till you get a better navigator and can move to a larger ship. A war schooner is the next step from the sloop, because you can capture a war schooner with a sloop without much effort. Once you are level 11 or 12, you can return to your brother and start the Dutch Gambit quest.
Other quests that you can do one you get a war schooner are Easy Prey and one of my favorites is to help a convict escape from prison. Usually they have huge treasures (similar to those that some damsel in the jungle have), much larger than the ones from bought treasure maps. But getting a convict out of prison onto your ship is tricky and can ruin your relationship with that nation, although there are ways to do this very easy without any bad consequences.