How likely is it that I would be caught and brought to justice? Would I be more likely to be killed or or wounded in the act than being brought to trial? Would it be a one way ticket, or would I have a realistic prospect to leave with my share of the booty whenever I wanted? If I did, would it be likely that the authorities would eventually catch up to me? And what are the realistic chances of making my fortune?
The short answer is that the average life span of a pirate during the Golden Age of Piracy after they mutinied or signed on with a pirate vessel was about one year. The old toast, "A merry life, and a short one, lads!" is very aptly attributed to people embracing the pirate life style.
It's easy to see the trend, when you start looking at the careers of famous pirates. Blackbeard's career as a pirate captain lasted less than two years, during which time he only took about 30 ships. And he is one of the most accomplished pirates to have ever lived.
So why did most pirates have such short careers?
First of all, sailing in and of itself was not exactly the safest profession. There were sailors who lived until they were too old and worn to sail anymore, but it was also not uncommon to lose ships during a big storm, or to just lose a man overboard from time to time. Accidents happened, both of the natural and the man-made varieties. During a voyage a ship was cut off from all contact with other people unless they happened to pass by another ship, and corporal punishment was the norm, especially on military vessels. Sometimes the bosun or the captain would get carried away while punishing a crewman. Some of these deaths were logged for what they were, and some of them were likely logged simply as "man overboard" and the crew was threatened into silence. When you add to that the fact that pirates are, by nature, also soldiers of a kind, the odds of living long enough to retire get even worse. Add to that that the penalty for piracy was death pretty much anywhere you went in the world, and your odds really aren't looking too hot. If you made enough of a nuisance of yourself, the navy would send ships out after you. Many pirates were caught and killed by these pirate hunters.
To further understand this number, we have to look at the reason why so many men turned to piracy. There are a few who set out looking for adventure, and a number who were basically pressed (forced) into service when their vessel was captured by a pirate ship (usually joining was voluntary, but if you had a skill that that the pirate ship needed, sometimes they'd take you whether you wanted to go or not), but most men became pirates because they had no other choice.
The people who financed ocean voyages at the time wanted to make as much money off of them as they possibly could. So, following a pattern that is as familiar to modern wage workers as it was to workers 300 years ago, they found ways to cut costs. Ships were often under manned, meaning that everyone on board had to work very long hours. There is also a finite amount of storage space on board a ship, meaning that every cubic inch of space you use to store food and necessities for the crew is space that you don't have to store cargo. You make money on cargo, but feeding your men is an expense. Accordingly, many business owners made the choice to send ships out with just enough starvation-level rations for the ship to make it to their destination. Starving men have a hard time thinking clearly. It was not completely uncommon for them to mutiny, kill the captain and probably the first mate, and spend a few days gorging themselves on whatever rations they had left. Whole ships of mutineers - pirates in the eyes of the law - starved to death because they over indulged in their rations, didn't have enough to make it to port, and were unable to capture another ship before they became to weak and hungry. Since these men lasted only a few weeks, it brings the average piratical survival time down by a good percentage.
Other hazards included loosing your navigator or your carpenter in the fight when you took another ship, and being either unable to repair your ship, or unable to navigate back to land. Sometimes pirates were just plain stupid. Alexander Selkirk, whose life was the inspiration for William Defoe's novel, Robinson Crusoe, was not an honest sailor like Crusoe, but a pirate. His ship had a bad case of termites and the rest of the crew wouldn't listen to him when he told them they needed to make repairs. They marooned him on an island off the coast of Chile with a few supplies and went on their merry way. Selkirk was rescued four years and four months later, but his ship foundered off the coast of Colombia a few weeks after abandoning him. Most of the crew drowned.
As far as whether you'd be able to become fabulously wealthy and leave your life of crime, I know of one historical account of that happening. A small group of pirates retired to an island in the Caribbean and became farmers. You also had a chance of retiring if you were a privateer, a pirate with official Letters of Marque issued by a country's government to attack the merchant ships of that country's enemy (like if Britain was at war with France, the British king might hire pirates to attack French merchant men and vice versa). In that case you might be able to retire to the country that issued you your letters of marque, as you would not be considered a criminal there. Of course, privateers could still be killed in battle or, like the highly successful Sir Francis Drake, die of diseases such as dysentery.
You may have heard that from time to time pardons were issued to pirates in the hopes that they would quit their evil careers if given the option. Some pirates took the pardon and lived peaceful lives thereafter. But a pardoned pirate is not necessarily a rich pirate. In fact, piracy didn't pay very well. After the Spanish stopped milking gold out of the South Americans, most captured ships were merchant men carrying goods like indigo, cotton, molasses, or slaves. You'd capture the ship, sell the goods somewhere at a cut rate, and the crew would split the payout equally with the captain typically getting a double share. This was more money than you'd make as a sailor, but is a far cry from the shower of gold and jewels pirates usually acquire in the movies. Bundles of fabric or barrels of fertilizer just aren't as glamorous as a chest full of doubloons, I guess. These guys still needed to make money, and the ex-pirate's marketable trades were sailing and fighting. Most of them ended up back on the water, and a sizeable portion went back to piracy before too long. Some pardons were more successful than others, when the economic climate was more forgiving.
So, long story long, you'd be lucky to live more than a year, and it's a toss up whether you'd be killed in battle, caught convicted and hung, or just ended up dying from bad luck or your own stupidity. Drink up me hearties, yo ho.