Pirating includes both the land profession Highwayman, and the sea profession Pirate.
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Pirating is often considered the most dangerous profession. An unprepared Pirate can be in a heap of debt in one bad trip, and many beginner have chosen pirate, only to discover this, and quit the game when they owe players several hundred gold. Despite these risks, it is quite easy to have a good tip and run off with a trader's good, or a hunters weapons.
The best way to pirate is to get a very powerful vehicle, but also with a good speed. Since a pirate only gets income by stealing cargo, they need to take as few weapons as possible. Often, a pirate will watch a player who has a valuable item, and have a Radar active. As soon as the player moves their item, the pirate checks the radar to see which route is most likely, and sends an interception force out.
Quite often, an Hunter on a good trip can pull in 3 or 4 bounties. the main issue is that most of these come from beginner players who are pirating, and can't afford the bounty. Instead of creating gold out of nowhere, the game now gives "loans" meaning the hunter does not receive the gold until the pirate can afford to pay the loan off, and they pay them off in order of when they received them.
List of bounties extracted from you
On the sea, the system changes somewhat. Since ships can be destroyed in battle, there is a greater risk of using more valuable ones. Also, because Ships have larger cargoes, pirates will load up with more weapons, and it is much more likely you will need weapons in order to beat them. This also increases the risk, because you are more likely to lose the weapons. Last of all, to make the risk even greater, Cannons up the ante incredibly. Your Cannons can't be stolen, but if a pirate has several good cannons and grape shots, it is quite unlikely your weapons will even be needed.
Also note that the main pirate of the sea is considered to be Manifest, who has a record of sinking the only 2 Ferries discovered, and countless valuables stolen.
It is quite unlikely a land pirate will make a lot of gold immediately. The only way to rake in big bounties is to buy very expensive vehicles, and get lucky enough to have greater power than the pirate.
The major pirates of the land are considered to be Adam, who has 3 out of the 5 top vehicles, and Oradow, who has 5 Bandits.