How to play a pirate
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Like all characters in the game, players get their ideas from the real world but it should be noted that characters need to be developed in the game so it might not be best to enter the game speaking a certain way. There is no set way for pirates to speak in Cantr, most of the time, speak like normal people but there are those that have certain accents or styles to their speech and so, to each their own. Due to real world stereotypes, people are likely to be suspicious of a sailor who wears an eyepatch and says "Arrr", so avoiding these clichés might help you to gain an element of surprise.
There is a wide variety of ships that can be built so your choice will not only be affected by your needs, but also by what you can afford. There are some ships in the game that that are fast and carry a lot, but are expensive and cheap slow ones. Most of the pirates preferred the darter and dinghy because of their unique characteristic of not being able to dock to, but that has changed now, all ships can be docked to, but only with certain other ships and so the darter is still currently the most popular ship.
It is good to be nearly untouchable, but speed is always great to have on your side to make speedy escapes. It all depends on what your needs, area or intentions are when picking a type of ship so think long and hard as to what you need.
Pirates with a crew might prefer a raker or a galleon since their storage capacity is vast, they are faster than the small vessels and can be further enhanced with the addition of masts and sails, and can be equipped with cabins and cargo holds to hold prisoners and protect loot. Their drawback is that they cannot dock directly to the shore and can be docked by various boats.
Risks and strategies
A pirate ship is most vulnerable right after undocking, so the perfect raid is timed right before the sailing tick takes place, allowing the boat to move away from the vicinity of the shore before the townspeople have time to retaliate. When a boat docks to a ship, it cannot be shaken off by any means so the situation might quickly turn dangerous.
Usually it's unlikely that several people are awake at the time of a pirate attack, that any of them would possess a key to a vehicle capable of docking to the pirate vessel, and even more unlikely that the defenders have more than one crowbar, if any, but in the worst case scenario, a pirate ship might be docked by for example a longboat with several people carrying crowbars and iron shields. The pirates may have tried to attack these people while in town and will be unable to strike again for a day, or even if they hadn't previously attacked these particular people, they might still be exhausted from hitting others and unable to deal significant damage. With luck, the docked people might be able to break through the lock in less than a day, forcing the pirates to retract to cabins, allowing the attackers to dock the ship back to the harbour and encourage the townspeople to board the ship. If the deck is stuffed full of loot, the people might be able to fill the remaining space so that pirates are unable to exit their cabins, leaving them trapped while the rest of the locks are broken. But a more likely scenario is that only one person is awake during the attack and even if they had a boat and a crowbar, they'll be too afraid to risk hanging along for what might turn out to be days.
If somebody is clearly awake during a pirate attack, it might be worthwhile to unlock the boat straight after undocking, and if someone comes after with a dinghy and docks to the pirate ship, they'll stumble right in through the door while attempting to break the lock. But this will require somebody to be awake to lock the boat before the intruder has time to realize they've walked into a trap. In this situation it's also good to have a cabin or a cargo hold to drag the intruder into, since he might still be able to break the lock from the inside and also to dock the ship back to the harbour.
Intimidating a lonely attacker might be worth while, since if they see a lot of pirates shouting threats at them, they might fail to realize that they're too tired to cause significant damage or have already used their one hit per day.
Violent vs. nonviolent approach
Hitting people is likely to make them more angry and makes you tired, which makes you more vulnerable to retaliation and dragging. Also, every move takes time. Hitting people can be profitable if someone is already wounded and likely to be easy to kill, or if wounding people enables dragging them to the ship or a seized building. It can also be used to create chaos and panic, but if people realize you aren't really able to kill anyone, the effect will wear off. A wise strategy would be to send a scout to live in the targeted town to find out everyone's fighting skill and strength (some clues can be acquired by trying to drag a person into some locked place for which neither the target or the dragger has a key) and who's carrying valuable keys or equipment. The primary target should be attacked by several pirates, preferably with a strong expert breaking through the target's defense to clear the way for the others. If the target is killed and keys are acquired, the pirates may either loot everything and sail away or to attempt to drag people into the gained building(s).
If you don't hit anyone and just grab what ever resources you find lying around, you won't be tired and even if someone was awake to hit you, they're unlikely to cause significant damage.
Radios have made piracy more difficult since towns can be warned without anyone having to travel between them to bear the message. Fortunately there are still a lot of regions that don't have this advanced technology. If a region has a lot of radios, well-equipped pirates should try to make themselves a vehicle radio receiver and be aware of the frequencies used on the region so that they can hear if nearby towns have been warned. A ship radio transmitter could also be used to broadcast false information to confuse the people, since there's no way of telling where a message comes from.