This is an awesome game, congratulations to the developer!
It is hard to get the hang of the game initially, but it is definitely “winnable”. A couple of tips for new pirates:
Maximize your sailing and fencing skills (e.g., unless you are a “trader”, set your charisma to “1”
. Sailing skills will help you close in on ships you wish to attack and help you elude ships that are more powerful than yours. Fencing skills will help you board other ships.
When you encounter other ships, compare their strengths and weaknesses against yours before deciding to attack or flee. In order to attack, you will need to outclass them in some attribute, be it cannons or manpower. If you outclass them in manpower, try boarding them. If you outclass them in cannons, use broadside attacks instead. If you don’t outclass them, then you should try to avoid the conflict. To avoid them, either flee or surrender. Add you sailing skills to your ship’s “rigging” rating and compare that to your opponent’s rigging rating. If your opponent’s rigging rating is higher, then you might want to consider surrendering, otherwise you should be able to outrun them.
When you capture a ship, consider seizing it (in other words swapping vessels) if it has better capabilities than yours. Once you get the hang of the game, a good tactic for getting wealthy (though a little risky) is to seize better vessels, sell them at the shipyard for a profit (by “buying” a lesser quality ship for a profit), and then going out and capturing a better quality ship, and repeating the process. One key to this is by to make sure your lesser quality ship has good “rigging” so you can pick and choose your battles (by outrunning ships you don’t want to fight). And when I say capture a better quality ship, you just need to have more men or more cannons so that you can win a battle via boarding or broadsiding respectively.
HTH!