Crook

Working Alone is Overrated

"There's no job that's best done alone, a trustworthy soldier by your side can be a life saver. So, you know what they say; watch my back, and I'll watch yours."

Gang Tactics

3rd-level Crook feature

You have advantage on melee weapon attack rolls against any creature if at least one non-Incapacitated ally is within 5ft. of you.

Additionally, you have Advantage on Intimidation (Charisma) checks against targets Grappled by you or an ally.

Word on the Streets

3th-level Crook feature

You can easily learn everything about a city's inner workings. You must spend seven days and 25gp to hire, bribe, socialize, and move around the city. Every day during that seven day period you may go explore, and roll an Intimidation (Charisma), Investigation (Intelligence), Perception (Wisdom), or Persuasion (Charisma) check to acquire information about the location from your GM, such as:

What the most profitable business in the city is? Where a faction's headquarters are? At which hours do certain people operate? Or, who may work for whom?

Sucker Punch

6th-level Crook feature

If your weapon deals Bludgeoning damage, it doesn't need the Finesse property to activate your Sneak Attack feature.

Back Alley Backup

9th-level Crook feature

After successfully using your Word on the Streets feature, you are known around town and the price of any hireling on that location is halved for you. Once per Long Rest you may go to a meeting point within said location and roll 1d2+1, you'll have that amount of hireling Thugs available. Hirelings granted by this feature return to their homes and normal routines when you take a Long Rest.

Additionally, every ally within 5ft. of you gains the effetcs of your Gang Tactics feature.

Hirelings count as allies for the purposes of all your class featrues.

Vita et Mors

13th-level Crook feature

If your Current Hit Points are half or less than your Maximum Hit Points; damaging a creature with your Sneak Attack feature grants you an amount of Temporary Hit Points equal to half of the damage dealt by it, which last for 1 minute. You can't use this feature again until you lose all the Temporary Hit Points granted by it.

Additionally, whenever you roll a 1 on a d6, you may reroll it.

Rattle 'em, Boys!

17th-level Crook feature

Any location in which you've successfully used your Word on the Streets feature, applies the feature's effects to another location nearest of it. Locations in which Word on the Streets is applied because of this feature do not repeat the process. The hireling Thugs you'd acquire from your Back Alley Backup feature are now Veterans instead.

Additionally, as long as at least 1 non-Incapacitated ally is within 5ft. of you, you and any ally within 5ft. of you can make 1 extra attack when taking the Attack Action. If any of your additional attacks would activate your Sneak Attack feature after it's already been used on the current turn, you may deal an extra 2d6 of the weapon's damage type on each of those attacks.