The Highwayman

Your skills are not honed through deliberate training, but instead by necessity. Personal greed, pride, hard times, plagues, famine, civil unrest, and the like you to a life of crime. You rely on dirty tricks and underhanded tactics to gain advantages wherever possible, anything to keep you drawing breath. Mercy and honour are often paid for in blood, and are not luxuries which your kind can afford.

Brigand Specialty

When you choose this archetype at 3rd level, you gain proficiency and expertise with Intelligence (Investigation) checks, and with land vehicles if you do not already have them.

Dishonourable

When you reach 3rd level, you learn two Dirty Tricks which you can use to help tip the scales in your favour. You gain three Dishonour points at this level, and you gain an additional point for every rogue level you take after this one. You learn one extra dirty trick at 9th level, and again at 13th, and 17th.

     You learn any two Dirty Tricks of your choice, which are listed below. Dishonour points can be spent to execute Dirty Tricks. Once a Dishonour point is spent it becomes unavailable until you finish a short or long rest. Once a rest is completed you regain all of your Dishonour points.

     Some of your Dirty Tricks require your target to make a Saving Throw to resist or break a feature's effects. The DC for these saving throws is calculated as follows; 

Dirty Trick DC = 8 + your proficiency bonus + your Dexterity modifier

Dirty Tricks

Flashing Knives.

     When you make a ranged weapon attack with a dagger but before you roll, you can spend up to three dishonour points to throw an addition dagger for each honour point spent. You must have enough daggers for every attack you make, and if you are attacking from stealth, only the first attack will have advantage. If you choose to attack multiple creatures, you can decide which one takes sneak attack damage, provided they are eligible for the damage.

Gouging Score.

     When you deal sneak attack damage to a creature with a finesse weapon that you are proficient with, you can spend 3 dishonour points to gouge the target, and cause it to bleed profusely. At the beginning of the creature's turn it takes 1d4 damage, this damage has no type and cannot be reduced. Undead creatures and creatures which have no blood are immune to this trick.
     A creature continues bleeding until it regains any amount of hit points, or uses an action to stop the bleeding. The damage from the bleed increases to 2d4 at 6th level, 3d4 at 9th, 4d4 at 12th, and 5d4 at 15th.

Grapeshot.

     When you make a ranged attack but before you roll, you can spend 2 dishonour points to make the shot explode before contact. You create an explosion 20ft square within your weapon's normal range which you can see. The point of origin for the cube must be on the side which faces you. Any creature in the square must make a Dexterity Saving throw, on a successful save the creatures take no damage. On a failed save a creatures takes damage. Damage is equal to two dice of the weapon you used to make the shot + your Dexterity modifier.

Hamstring.

     When you hit a creature with a melee weapon attack using a finesse weapon which you are proficient with, you spend 1 dishonour point to temporarily impair your target. The target of the attack has their walking speed halved until the end of their next turn.

Pocket Sand!.

     As an action, you can spend 2 dishonour points to try and throw a pocket full of sand, powder, dirt or other similar substance into the eyes of another creature. Make a Dexterity based attack with a range of 5/10 + your proficiency bonus against the creature. On a successful hit, the creature is blinded until the start of your next turn or until it takes damage.

Roguish Parry.

     As a reaction to a successful attack against you, you can spend 1 dishonour point to attempt and deflect the attack provided you can see the creature targeting you. Add your proficiency bonus to your AC for one attack, if this brings your AC above the attack roll, you may attempt to deflect the attack to a creature within 5ft of you. If the deflected attack can hit the creature you target, it deals damage as normal against the new target. If you do not redirect the damage the attack does no damage to you as normal.
     Starting at level 10, your awareness for danger heightens. You gain the ability to deflect attacks even from creatures you cannot see.

Aim for the Eyes.

     When you make a ranged weapon attack against a creature with eyes, you can spend 1 dishonour point to try and make the target flinch. Regardless if your attack hits, the target must make a Constitution saving throw, on a failed save the target loses its reaction until the start of it's next turn.

Dodging Gallows

Starting at 9th level, your hit point maximum increases by a number equal to your rogue level. Your hit point maximum cannot be reduced below this number by any means. Additionally you can hold your breath for a number of minutes equal to 1 + two times your Constitution modifier.
     Starting at 14th level, you gain advantage on death saving throws.

Emboldened Figure

Starting at 13th level, you become comfortable donning heftier armor, and understand how to wear them with a daring audacity. You gain proficiency with medium armor if you do not already have it, and you ignore the Dexterity Modifier limit for any medium armor you wear.

Champion of Cruelty

     By 17th level, you have learned to wield weapons with maximum efficiency, perfecting each strike to inflict as much pain as possible. Whenever you make a ranged or melee attack you roll two of the weapon's damage die instead on one to determine damage. To benefit from this feature you must attack with a weapon you are proficient with. This feature does not affect your sneak attack damage.