Criminal - Burglar (Grim Hollow)

Burglars break into and steal from houses,
storefronts, and warehouses, primarily operating
out of major cities and ports. While thieving is
a risky pursuit, the hardest part can be finding
a buyer for rare and valuable items. The more
unique the good, the more likely its original
owner will want it returned, cutting your profit
margin considerably.

Goods and valuables generally need to be sold
through a fence: someone who will purchase your
stolen goods, sell them to unknowing customers,
and take a cut of your profits.

Rank 1 - Snatcher

Breaking into homes in the lower end of town is
generally your trade. Authorities only worry about
civilians with the power to cause a stir; everyone
else is on their own. Locks in this end of town are
easy to pick, if there is a lock at all. For the same
reason, though, there is less to steal.

Holdings:

A safehouse in the poor district, used to store
stolen goods and serving as emergency lodgings.
You have blueprints of a grand estate including
secret entrances and passageways.

Progression:

You rob a well-to-do store in a reputable district,
gaining notoriety and a big payday.

Rank 2 - Burglar Specialist

Working in a team, while risky, allows for heists
that would be beyond the reach of any oneburglar, no matter how skilled. Increasingly,
when someone has an ambitious crime planned
and needs to assemble a team of “the best,” they
reach out to you.

Holdings:

A team of specialist thieves who operate under
your instruction to execute more ambitious heists.
A contact working inside an establishment
which you plan on robbing, who provides you
information on the routine of the occupants, the
location of valuable items, and escape routes.

Progression:

Membership in an established Thieves’ Guild in a
major city or town.

Rank 3 - Heist Master

Your skill as both a burglar and a leader has
grown considerably over time. Whether by
virtue of your own confidence or a message
from the divine, you believe that you are capable
of executing a major heist, with the right
preparation and henchmen of course. Will it be
a priceless painting you have been tasked with
acquiring for a prospective buyer? A slovenly
prince whose private affairs you seek to meddle
in, having acquired his signet ring?

Holdings:

You hold a senior position in the Thieves’ Guild,
instructing junior members in lockpicking,
housebreaking, and evading law enforcers.
You uncover evidence of an attempted
assassination on the life of a noble whose estate
you robbed.

Progression:

You orchestrate a large-scale heist to rob the
estate of a local noble.

Rank 4 - Prince of Thieves

You have squirreled away enough gold to live
comfortably for the rest of your life. However, you
now steal to satiate a greater motivation through
the exchange of private information, blackmail,
and the acquisition of rare and powerful artifacts.
After all, knowledge is power, and you’ve risen to
a level where power is mandatory.

Holdings:

Your own estate with a household of staff,
acquiring and selling rare and valuable items
through your own circle of thieves, fences,
and buyers.

Applied Leverage 

When you make a Strength
(Athletics) check to force open a door or container,
you may add your profession die to the roll.

Bounty Hunter

Whenever you make a Wisdom (Survival) to track
Criminals, you can add your Profession Die.

Charity Case

When you make a Charisma
(Performance) check to fake an illness, injury, or other
condition, you may add your profession die to the roll.

Contortionist

Whenever you make a Dexterity or Dexterity
(Acrobatics) check to squeeze through a small
space or escape bonds, you can add your
Profession Die to the roll.

Copycat

Whenever you make an Intelligence or
Intelligence (Forgery Kit) check to forge or create
a document, you can add your Profession Die
to the roll.

Disciplinarian

Whenever you make a Charisma (Intimidation)
check while issuing a command to an individual
of lower rank within your background, you can
add your Profession Die to the roll.

Drunkard

Whenever you make a Constitution check to
determine if you will throw up, pass out, or how
severe a hangover is, you can add your Profession
Die to the roll.

Elusive

Whenever you make a Dexterity (Stealth) check
to hide or blend into a crowd of humanoids
that share your background, you can add your
Profession Die to the roll.

Gambler

Whenever you make a Dexterity (Sleight of Hand)
or Wisdom (Perception) check to cheat at a game
or catch someone else cheating, you can add your
Profession Die to the roll.

Grifter

Whenever you make a Charisma (Deception)
check, and are attempting to pass off a fake object
as authentic, you can add your Profession Die
to the roll.

Heister

Whenever you make a Wisdom (Perception)
check to spot traps, sentries, and other security
measures, you can add your Profession Die
to the roll.

Impressionist

Whenever you make a Charisma (Performance)
or Charisma (Deception) check to mimic the
mannerisms, voice, or appearance of another
humanoid, you can add your Profession Die
to the roll.

Interrogator

Whenever you make a Charisma (Intimidation)
check to extract information from an enemy who
is restrained, you can add your Profession Die
to the roll.

Looter

When you make an Intelligence (Investigation)
roll to find hidden valuables, you may add your
profession die to the roll.

Menacing Presence

Whenever you make a Charisma (Intimidation)
check, and are interacting with Academics,
Common Folk, or Seafarers, you can add your
Profession Die to the roll.

Nimble Fingers

Whenever you make a Dexterity (Thieves’ Tools)
check to pick a lock, you can add your Profession
Die to the roll.

Quick Fingers

Whenever you make a Dexterity (Sleight of Hand)
check to place a small object on a humanoid or
sneak something into their food or beverage, you
can add your Profession Die to the roll.

Renowned

Whenever you make a Charisma (Persuasion)
check, and are interacting with Military,
Outlanders, or Criminals, you may add your
Profession Die.

Ropesman

Whenever you make a Strength (Athletics) or
Dexterity (Acrobatics) check to climb, move
along, or jump onto ropes, you can add your
Profession Die.

Sentry

Whenever you make a Wisdom (Perception) check
while on watch duty or defending a fortification,
you can add your Profession Die to the roll.

Sticky Fingers

When you make a Dexterity (Sleight
of Hand) check to snatch something quickly, you may
add your profession die to the roll.

Urban Sprinter

Whenever you make a Strength (Athletics) or
Dexterity (Acrobatics) check while running away
from a pursuer, or pursuing someone else, you
can add your Profession Die to the roll.

Vacant Expression 

When you make a Charisma
(Deception) check to feign ignorance and you are
interacting with an Academic, Aristocrat, Clergy, or
Militarist, you may add your profession die to the roll.