Serial Killer

Sometimes a rogue does what they do because they love to do it, not because there's coin. These rogues excel at extracting information about and from their target. Given enough time and obsessive, sociopathic stalking, the Serial Killer can learn much about someone, enemy or friend. 

Stalker's Observation

You have a keen eye for tracking people, especially when you've chosen a target. Starting at level 3, you gain advantage on Wisdom (Perception) checks when spotting your target and Intelligence (Investigation) checks when tracking and following your target. 

Analytical Gaze

Choosing this archetype at level 3 lets you use your knowledge of previous victims to quickly scan a target's physiological or psychological weaknesses. A number of times equal to your proficiency, you can choose make a Wisdom (Insight) or Wisdom (Medicine) check against an enemy you can see as a bonus action. Depending on what check you make, this feature gives different effects.

 

Insightful Analysis

As a bonus action, make a Wisdom (Insight) check against the target's AC as you peak into the psychology and fighting style of your target to find the perfect moment to strike. On a fail, gain no benefit. On a success, gain advantage on your next weapon attack against the target.

Medical Analysis

As a bonus action, make a Wisdom (Medicine) check against the target's AC to find weak points in their physiology and cause them lasting pain. On a fail, gain no benefit. On a success, deal an additional 1d4 piercing damage on your next weapon attack against the analyzed target and cause them to bleed. Unless the target gets healed or uses an action to stop the bleeding, they'll take another 1d4 damage at the end of each of their turns.

Menacing Extraction

Starting at 9th level, gain proficiency with Charisma (Intimidation). Additionally, when interrogating or attempting to extract information from a target, they can use a charge of Analytical Gaze to gain advantage on Wisdom (Insight) checks against the target for the duration of the interrogation. Furthermore, coercing the target or succeeding a Charisma (Intimidation) check gives you advantage on the rest of your Charisma (Intimidation) checks against the target for the duration of the interrogation.

Vicious Precision

Starting at 13th level, your predatory instincts and patience in stalking prey grant you unparalleled precision in combat. When you hit a creature with a melee attack that qualifies for your Sneak Attack, you can reroll any 1s and 2s on the damage dice. You must use the new rolls.

Additionally, once per short or long rest, when you hit a surprised creature with a melee attack, you can choose to deal maximum damage with your Sneak Attack dice.

Master of Terror

You have become a true master of stealth and death, striking fear into the hearts of your enemies and leaving no trace behind.

At 17th level, you no longer need to make stealth checks when moving through shadows and have advantage on Dexterity (Stealth) checks even if you're only lightly obscured.. Additionaly, once per long or short rest, pick a target within 60ft of you to become your victim and have them make a Wisdom save against your Spell Save DC (8 + Proficiency Bonus + Intelligence Modifier). If the target fails, they become your victim. After successfully hitting your victim with a melee attack, they become frightened of you for 1 minute and the timer resets whenever you land another melee attack. While frightened in this way, you deal max damage with your melee and sneak attacks against the target. The condition ends when the 1 minute passes without interruption or the target goe unconscious. If the target succeeds, however, nothing happens.