Dave, read this (it's my old post)
Your Hero at the beginning cannot hit his own nose becasue he has extremely bad starting skills. So don't try to fight sea battles.
So how to get some money:
1. Buy yourself a pistol and 15-20 bullets. Don't forget to equip it. If there is no seller of pistols go to the church. Someone there may be selling stuffs too.
2. Go to the moneylender. Click several times to talk with him untill he gives you the quest to find his lost jewel.
3. Go to the governers and ask for work. He will give you the quest to kill the robber gang in the jungle. The "gang" for now is just 1 man so you will be able to kill it and to get soem money as reward. At the same time you must start learning to fight. But beware if you see more then 1 rogue in the jungles. Better run away then (they are not the quest "gang" anyway). When you kill the robber stand exactly where his feet are and press 1 to loot the body (this way you can loot every body). Meanwhile if you find a cave loot the chests inside. It is completely safe there providing you don't step in the white glowing light. The big caves has 3 chests and the small caves (grotto) 1 chest. AND do not step in the white glowing light
4. Return to the map just outside the city gates and start looking for the moneylender jewel. Turn off from the options the foliage and press Tab to go in 1st person view. Then start to look around. You probably will not need more then 5 minutes to find it. The moneylender will give you from 1000 up to 4000 golds (on captain level).
5. Return to the town and start searching for open houses. Enter each open house and if it is empty loot everything you find. Sell the loot.
6. With min luck you probably will have 4000-5000 golds now.
7. Go for the tavern now and start looking for officers. If you find good officer bargain for his price. Your top priority are fighter and treasurer. The fighter will allow you to kill (and loot) the robbers in the jungle and the treasurer will alow you to earn money by trading. Don't hire other officers except if you find some officer with extremely good stats.
DO NOT GAMBLE. You will lose your money if you don't save and reload. And if you do save and reload everyone quite soon will refuse to play with you. At the same time you NEED the posibility to gamble so you can raise your "luck" skill later. But do it later - when you can afford to lose money.
8. When hiring officers it is good to check if they are good or bad natured. This is shown as "reputation". If you plan to be the "good" guy the bad officers will leave you at some time when their loyalty drop to zero. But of course you can hire some temporarily officer if you like.
9. Go to the store and ask if the owner will hire your ship. If he agree look where is the destination port. If it is close enough agree, go to the port and sail avoiding pirates and enemies. Before sailing hire soem crew from the tavern. No need to repair the ship. Yet. Before sailing you can go to port office and ask for work. Agree if you get the task with the forgotten ship's logbook. When at the sea look be carefull about a ship with green sails - this is your guy.
If the store owner or you decline read p.10
10. Sleep at the tavern and loot the room.
10. Repeat 1-9 only without the governor. He probably will give you the quest to deal with smuglers and you are not ready for this.
11. Meanwhile it is good to train swordfigting dueling in the tavern. You learn to fight, raise skills, loot bodies and gain positive reputation. The drawback of this is they can steal your money. So either save and reload OR if you are like me and don't like to save and reload then leave all your money in the moneylender or in the officers if you have any.. Keep in your pockets not more then 100 golds. If you have less money the option for the fight will not appear.
