Beggar

Alternatively: Vagrant.

Despite the efforts of certain religions and a few socially conscious government officials, poverty is present in many parts of Adra, but in particular, in the cities of Adra, where money is relied upon more than in most other places. Folks who can't find a way to keep up with making money have to feed themselves somehow, and many turn to begging. Beyond contributions from strangers, beggars can make money by joining Beggars Guilds, which see dozens or hundreds of beggars running jobs or providing information for reimbursement from interested parties.

          Beggars pick up plenty of tricks and skills out on the streets that they can use in other pursuits, including a life of adventuring. Beggars who become adventurers are likely to never quite feel safe in their new position, and might maintain some of the habits that kept them alive when they lived on the streets. Whenever a party arrives in a new town, they probably will make contact with the local beggars to establish a rapport and get the lay of the land.

          I Am But a Wretched Cur: Beggars are looked down upon, ignored, ostracized, and while most would despise this condition, you take advantage of it. Whenever an opponent in battle would attempt to directly attack you, before they do, roll 1d6. On a 1, the opponent will ignore you because of your wretched aura and choose another target for their aggression. If you are the only target left standing, or the only possible target for whatever reason, then this feat does nothing.

If you choose Beggar, you gain the following:

~Either a +1 to your Constitution score or a +1 to your Charisma score~

~A Skill Proficiency in either Survival or Persuasion~

~A Tool Proficiency with a Disguise kit~

~The following items: A disguise kit, a pewter cup, a waterskin, a wretched cowl, and a shoe with 3sp stuck in it~

~I Am But a Wretched Cur feat~

Confidence Artist

Confidence artists, con artists for short, are lowlife criminals who pride themselves on tricking folks to part with their money. Confidence artists range from small time petty thugs running ball and cup scams in the merchant district all the way up to well dressed suave somebodies who run long cons for thousands of gold. Con artists aren't dangerous to your life, usually, but they sure are dangerous to your pockets.

          Con artists like a life of adventure, because it gives them a way to supplement their income, allowing them to focus only on the biggest of scores. Furthermore, it gives them a good cover, and keeps them constantly moving so they never get pinned. Con artists who become adventurers are probably always looking for easy marks, even when they shouldn't - they are handy to keep around though, as they will usually let their party members know when someone else is trying to take them for a chump.

          Sir, I Left My Keys in My Car: You are an expert at separating people from their money willingly. You may spend 1 hour in a settlement coning people to the best of your ability, at the end of which you gain 5d12+5 sp. However, you have a 1 in 6 chance every time you do this of ruffling someone's feathers mightily, at which point you will have to run from the guards and lie low for a while. You can only perform this activity once per long rest, and after you have performed it 5 times in the same settlement, word has spread not to trust you, and the con no longer works in that town.

If you choose Confidence Artist, you gain the following:

~Either a +1 to your Charisma score or a +1 to your Dexterity score~

~A Skill Proficiency in either Deception or Sleight of Hand~

~A Tool Proficiency with any one Gaming set~

~The following items: A gaming set, tools for your usual con, a dagger, an inconspicuous set of clothing, and a belt pouch with 12sp~

~Sir, I Left my Keys in My Car feat~

Cutpurse

Alternatively: Robber, Pickpocket, or Burglar.

Cutpurses are hit and run thieves who move quickly to a target, cut their purse or bag, or otherwise shake them down before they have a chance to react, and then when they have the goods, run off as fast as their feet can carry them. Some cutpurses are a little more stealthy, and a few even rob from peoples homes instead of their persons. Often, cutpurses are low level thieves who work for and report to much more influential criminals.

          Cutpurses usually do what they do because they don't have another option - when one presents itself, like more legitimate work with an adventuring party, they often take it. Adventurers who used to be cutpurses will probably always keep an eye out for strangers, looking out for any other cutpurses or pickpockets in larger cities. Despite this, they know what it's like to be hard up, and they tend to show more sympathy for common criminals than your average adventurer.

          I Always Get My Mark: You aren't going to take failure lying down; you probably have debtors to pay back after all. Even when you fail to pickpocket or take something using a Sleight of Hand check, you still take the item, but you have been discovered. Furthermore, you can make a Deception check with advantage to quickly get out of the situation, though the person will realize soon that they've been duped.

If you choose Cutpurse, you gain the following:

~Either a +1 to your Dexterity score or a +1 to your Strength score~

~A Skill Proficiency in either Sleight of Hand or Stealth~

~A Tool Proficiency with either Thieves' tools or a Disguise kit~

~The following items: Either thieves' tools or a disguise kit, a dagger, a set of caltrops, a black cloak, and a belt pouch with 12sp~

~Cutpurse feat~

Forger

Bureaucracies, militaries, and the nobility use a series of signet rings, medallions, seals, paperwork, and insignia to ensure that their messages and mandates are official and beyond doubt. Still, there are those that do their best to make sure that there are no things which are beyond doubt - professional forgers who create fake replications of documents and other kinds of insignia. These forgers stay mostly away from the heat, working out of quiet offices, and they tend to be paid well for their work by the crime families and professional criminals that utilize their services.

          Forgers might sometimes be contracted out by adventurers, who need to make use of their services in order to gain papers, to get access to a place they aren't supposed to usually. Forgers that are especially skilled might be tapped to work permanently with a successful adventuring party. Characters who used to work as forgers will likely always be looking for ways to use their skills - when they make a good forgery, they will likely keep it in their collection, or they may even sell them after they are done.

          Trust Me, I'm Legit: You have been doing this long enough to know when you have seriously screwed up. When making a forgery, you can ignore the Secret check and make a forgery as a normal check once per long rest, allowing you to have a second chance in case you make a terrible forgery the first time. Furthermore, while it would normally take time to make a convincing forgery, when pressed to do so, you can make a forgery in 1 minute, so long as you have your forgery kit with you, though you make it with a -3 penalty.

If you choose Forger, you gain the following:

~Either a +1 to your Dexterity score or a +1 to your Wisdom score~

~A Skill Proficiency in either Perception or Sleight of Hand~

~A Tool Proficiency with a Forgery kit~

~The following items: A forgery kit, a fake piece of identification, a logbook, a spiffy cap, and a belt pouch with 12sp~

~Trust Me, I'm Legit feat~

Gambler

Gambling for most people is the occasional past time or a little habit, but for some, they are either so good at gambling, so hopelessly addicted to it, or some combination of the two, that they gamble fulltime. These professional gamblers might play games that rely on a good deal of skill, like certain card games, or they may make sure that the games go their way no matter what, using the wits or tricks that they need.

          Often, gamblers are in need of a sure way to get some money, when they have debts or they've run out of money, or maybe when they need money for a big game. Adventuring can provide a stable income that isn't so tied to the roll of a dice. Gamblers who become adventurers will probably look for the action in any settlement the party visits, and they might even try running a "friendly" game with their party members.

          You Gotta Know: Many believe gambling is merely pure chance, but you know better. Because of your skill at gambling, you gain advantage on any check that abstracts away a gambling game. Furthermore, when playing Dragon's Gambit (Farkle), you always have one lucky die that you can switch to any face when you have rolled the other 5. This does not represent cheating, or a trick die, but a genuinely lucky die.

If you choose Gambler, you gain the following:

~Either a +1 to your Charisma score or a +1 to your Dexterity score~

~A Skill Proficiency in either Deception or Sleight of Hand~

~A Tool Proficiency with either a Dice set or a Playing Card set~

~The following items: Either a dice set or a playing card set, a lucky rabbit's foot, a bottle of mead, a spiffy cap, and a belt pouch with 1d20sp~

~You Gotta Know feat~

Graverobber

Alternatively: Ghoul.

In the world of Adra, there are always those who have a need for dead bodies. Necromancers, scholars, and creeps always find something to do with fresh bodies, and graverobbers do their best to supply the need. Furthermore, sometimes graverobbers don't even care about the bodies, but instead what the bodies have on them - gold, trinkets, heirlooms - all valuable, and all can be pawned away to the right individuals.

          Adventurers more often than anything have conflicts with graverobbers, sometimes following leads in cemeteries to find those responsible for the defiling of graves. When graverobbers are rehabilitated, or simply get out of the game before it's too late, they might be drawn to a life of adventuring to give them a new life. Adventurers who used to rob graves are likely to show a frightening lack of respect for graves in their life of adventuring, particularly when inspecting one could bring great rewards or save lives.

           Night Robber: A good graverobber does all of their work in the dead of night, and you can apply this skill to your adventuring career as well. When you are outdoors and it is nighttime, you treat dimlight as darkness for the purposes of your stealth - and in darkness in the outdoors, you utilize shadows to be considered hidden even from creatures with Darkvision, taking advantage of their black and white sight.

If you choose Graverobber, you gain the following:

~Either a +1 to your Constitution score or a +1 to your Dexterity score~

~A Skill Proficiency in either Stealth or Athletics~

~A Tool Proficiency with Thieves' tools~

~The following items: A sturdy shovel, thieves' tools, a crowbar, a black tunic, and a belt pouch with 12sp~

~Night Robber feat~

Hired Muscle

Alternatively: Thug, Bravo, or Goon.

In the vast criminal underworld of Adra's cities, every gang, family, and crime organization needs plenty of hired muscle - just big dumb thugs who sit behind them looking all menacing-like. Hired muscle are usually just there for protection, but are sometimes sent in to intimidate rivals and witnesses, or when push really comes to shove, act as the front liners in any violence conflicts between gangs or with constables.

          Hired muscle are usually used like pawns by the organizations and individuals that they work for, and when they are of no more use, they get thrown away like pawns. As such, many get wise to their unfortunate fate before its too late, and join a career in adventuring, one that might better make use of their muscle. Former goons who become adventurers are likely to let their other party members do the talking with others, more comfortable with being the strong silent type.

          Ominous Aura: In your experience, often words can get in the way of the universal language of fear. When others in your party are making Intimidation checks, once per Long Rest you can make an Intimidation check of your own, and if you succeed, you add 2d6 to their check. Furthermore, in combat, when your opponents have to make a saving throw against the Frightened condition for any reason, they take a -2 to their saving throw. Finally, you take no penalty to Intimidation checks against creatures that can't understand your language or speech.

If you choose Hired Muscle, you gain the following:

~Either a +1 to your Strength score or a +1 to your Charisma score~

~A Skill Proficiency in either Intimidation or Athletics~

~A Tool Proficiency with any one Gaming set~

~The following items: A gaming set, a simple weapon, knuckle dusters, a badass belt, and a belt pouch with 12sp~

~Ominous Aura feat~

Outlaw

Alternatively: Highwayman.

Some folks are just plain bad. Whatever unlucky life pushed them to thuggery and crime, outlaws are folks who use violence and intimidation to get what they want, often in bands of other outlaws. Outlaws tend to keep to the highways, roads, and countryside, where any real law isn't to be found in abundance. There, they prey on caravans and farmers, robbing, killing, and shaking down anyone in their path.

          Outlaws run afoul of adventurers all the time - and in doing so, some get shown mercy when they are defeated by those more powerful or more clever than they are. Outlaws might try to turn a new leaf, and live a life of peace, or they may just be looking for a higher class of gang to work with. Outlaws who become adventurers will constantly fight their urge to see an easy mark for the taking, and they may constantly deal with others judging them for their past wrongs, even if they are moving past them.

          Outline of an Outlaw: Outlaws have a certain way of recognizing their own kind, and this pays off when out in the wider world. When other criminals see you, and they would have made an attempt to steal, con, scam, or attack you, they instead leave you, and anyone you are with alone. Furthermore, you can make a DC 13 Insight check to detect if anyone you come across is a career criminal (though they are aware that you make this assessment). At level 7 and above, criminals will not only ignore you, but they will actually offer their services to you if you need them. This does not prevent criminals working for factions that you are in conflict with from making moves against you.

If you choose Outlaw, you gain the following:

~Either a +1 to your Constitution score or a +1 to your Charisma score~

~A Skill Proficiency in either Intimidation or Stealth~

~A Tool Proficiency with a Poisoner's kit~

~The following items: A simple weapon, a set of caltrops, a poisoner's kit, leather armor, and a belt pouch with 12sp~

~Outline of an Outlaw feat~

Pirate

Alternatively: Raider or Marine.

Coastal communities tend to be richer than inland ones, well supplied with fish and bolstered by trade, these towns make great targets for pirates who use hit and run tactics to attack a lightly defended community, make off with as many goods as possible, and run off before soldiers are able to respond to the threat. Pirates also apply this same strategy to the raiding of merchant ships. The threat of pirates consistently puts pressure on oversea trade routes and on coastal communities to adapt and respond as best they can.

          Pirates might sometimes make some decent scratch, when they get lucky, but plenty of times, pirates are fighting a constant battle against breaking even, with only the most skilled and tenacious crews taking any real scores. Many look to other lines of work, like adventuring, to give them a better chance of breaking even before they die. Pirates who retire to become adventurers will probably be drawn to adventures that take the party on the seas, and might have a certain lingo with others integrated with pirate economies.

          Hit and Run: Raiders excel at descending upon their prey and running for the hills before they know what hit them. Once per short rest, you may attack and disengage with the same action. If you gain Extra Attack, you can attack multiple times and disengage with the same action.

If you choose Pirate, you gain the following:

~Either a +1 to your Dexterity score or a +1 to your Constitution score~

~A Skill Proficiency in either Acrobatics or Athletics~

~A Tool Proficiency either with Cartographer's tools or Navigator's tools~

~The following items: Either cartographer's tools or navigator's tools, a simple weapon, an empty sack, a helmet, and a belt pouch with 12sp~

~Hit and Run feat~

Smuggler

Alternatively: Bootlegger.

There are plenty of restrictions in the various polities of Adra on certain goods - these might be certain drugs, weapons, or embargoed goods - they might be outlawed for moral reasons, or to restore a trade deficit. No matter what it is, the restriction almost always creates a demand that is fulfilled on the black market, and to get these goods from point a to point b, you need a smuggler, a professional who specializes in illegally transporting goods.

          Smugglers sometimes look for adventurers to help them with their profession - not always moving drugs and illicit substances, sometimes smugglers transport vital trade goods to regions that need them badly. If smugglers join the ranks of adventurers, they are likely to push for jobs that make use of their unique skill set. They might also be more comfortable with illicit activities than your average adventurer.

          Holdout Hero: The key to a good smuggler is holding out without sweating it. You have a subdiscipline in Sleight of Hand on Concealing an object on your person. Furthermore, you have a special spot that you can hide one item of 10lbs or less, and it can't be discovered with anything other than magic.

If you choose Smuggler, you gain the following:

~Either a +1 to your Dexterity score or a +1 to your Charisma score~

~A Skill Proficiency in either Deception or Sleight of Hand~

~A Tool Proficiency with a Disguise kit~

~The following items: A simple weapon, a disguise kit, something illegal somewhere, a coat with many pockets, and a belt pouch with 15sp~

~Holdout Hero feat~