Delinquents are the kind of people you don't make eye contact
with when you walk down the street. The kids who when you
see bunched up in an alley, or crowded around a clerk in a
store, you know to just keep on walking. Rogues who travel
down this path of expertise are masters in the art of really
making their neighborhoods their bitch, and showing those
who pushed them down what's what.
Window Shopping
Upon reaching 3rd level, you've begun to master the streets
like very few others can, and in doing so, have learned a
number of techniques to match. You gain the ability to over
the course of a short rest, scan a square mile of town or city
for the shops and establishments that would hold the most
valuables. This activity is considered light activity for the
purposes of completing your short rest. Upon completing this
short rest, you are aware of any businesses or establishments
that have high gold value in goods on display, and if so, you
learn what those items are and their individual values.
Breaking and Entering
Additionally at 3rd level, you gain proficiency in improvised
weapons. When you hit a creature with a melee attack using a
improvised weapon, simple weapon or unarmed strike, you
can apply your sneak attack dice to the damage roll if the
creature is surprised or you are in a grapple with the creature,
and you do not have disadvantage on the attack. You may now
also use all previously available ways to deal sneak attack
damage with your unarmed strikes as well as improvised
weapons. Additionally, When dealing damage to objects, you
always apply your sneak attack damage to the damage rolls.
This rolled sneak attack damage does not count against the
one iteration of sneak attack you are normally allowed to
apply to attacks per turn.
Sucker Punch
Upon reaching 9th level, you have began to really get the hang
of catching people off guard. You know how to take
opportunities and strike when it's least expected to get a one
up on your opponent. When initiative is rolled, you may roll a
Charisma (Deception) check as well, against the initiative rolls
of all other creatures within the combat. Any creature thats
initiative is less than your Deception roll is considered to have
been surprised by this engagement.
Break Off
Once you've reached 13th level, when you hit a creature with
an improvised weapon that is the same size category as them
or smaller, you can choose to attempt to break the weapon off
on them. If the damage you deal would also break the item,
the items is destroyed, and the attack deals additional damage
equal to the hit points the item had before the attack was
made.
Full Fledged Brawler
At 17th level, your ability to hold your own in a fist fight is
unmatched. You can now apply your sneak attack damage to
any unarmed strike or improvised weapon attack that you
make. When you hit a creature with an unarmed strike or
improvised weapon that is surprised, or grappled, the attack is
considered a critical hit.
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