Con Artist

You thrive in exploiting a person's trust in order to reach your goals and gain leverage above the rest. Rogues of this archetype are charismatic and charming, constantly delving into conversations and leading them down the desired path. Be it money, influence, or something else entirely - the target of a Con Artist seldom knows who stabbed its back after all is said and done.

Sharp Tongue

Starting at 3rd level, you are proficient in Deception and Persuasion ability checks. Additionally, while in combat, you may roll Deception and Persuasion ability checks with advantage.
You also receive a pool of 'Restate' points, which can be individually spent to reroll a Deception or Persuasion ability check.
You must keep the new result and cannot reroll the same check more than once.
The pool refreshes after completing a Long Rest.

At 3rd level, you gain one 'Restate' point. Gain another point at 9th and 15th level, respectively.

Fatal Presents

Beginning at 3rd level, you are in possession of and proficient with Alchemist's supplies and Cook's utensils.
You also know how to craft a plethora of consumables, which increase in effectivity as your experience grows.
You can only craft one such item per day and hold your Intelligence modifier + 3 of them at a time.
The sell value of such an item is half the price of its components combined sell value.

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Craft consumables using a carrier and a property.
Properties and only be integrated into carriers that you have created yourself.

At 9th and 15th level, crafted consumables become 'Higher' and 'Supreme' items, respectively, with heightened effects.

Carriers:
Potion - Ingestible in and out of combat with immediate effects; requires a glass bottle, water, herbs, a colouring agent and Alchemist's supplies to be crafted.

Candy - Ingestible in and out of combat with effects showing after 5d10 + 10 minutes; requires sugar, fruits, a colouring agent and Alchemist's supplies to be crafted.

Bread - Ingestible outside of combat with effects showing after 8-12 hours; requires water, grain, yeast and Cook's utensils to be crafted.

Properties:
Cutting - Causes internal bleeding after ingestion, dealing 1d8 + your Intelligence modifier Slashing Damage at the start of the consumer's turn. At the end of its turn, it must succeed in a DC 14/16/18 Constitution saving throw or the effect persists. Can only be used on Potions.

Infected - Causes creeping organ malfuncture after ingestion, dealing 1d4/1d8/1d12 Poison Damage to the consumer every hour and applying the Poisoned condition. While under the effects, the consumer cannot heal naturally. It has to be magically cured (e.g. by Lesser Restoration or similar spells) or ingest a consumable with the 'Cleansing' property to shed the effects. Can only be used on Candy and Bread.

Tensing - Causes muscles and tendons to lock up after ingestion, applying the Paralyzed condition to the consumer. It has to be magically cured (e.g. by Lesser Restoration or similar spells) or ingest a consumable with the 'Cleansing' property to shed the effects. Can only be used on Candy and Bread.

Enticing - Causes relaxation of mind and body, applying the Charmed condition to the consumer. It has to be magically cured (e.g. by Lesser Restoration or similar spells) or ingest a consumable with the 'Cleansing' property to shed the effects. Can only be used on Candy.

Tiring - Causes the body to slowly numb away as nightmarish sleep takes hold, applying the Unconscious to the consumer. It sleeps for 1d4/1d6/1d8 days unless magically cured (e.g. by Lesser Restoration or similar spells) or being fed a consumable with the 'Cleansing' property to shed the effects. While asleep, it does not regenerate hit points, exhaustion or spell slots and continues to grow hungry and thirsty, unless it is frequently fed. Can only be used on Bread.

Cleansing - Causes harmful substances to be shed from the body after ingestion, freeing the consumer from the Poisoned condition and effects of consumables with the 'Infected', 'Tensing', 'Enticing' and 'Tiring' properties. It also gains Immunity to being Poisoned for 1 minute/hour/day. Can only be used on Potions.

One-Way Mirror

Starting at 9th level, after having conversed with a creature for at least an hour, Insight ability checks against that creature are rolled with advantage.
All of its Deception, Persuasion and Insight ability checks against you are rolled with disadvantage.

Hidden Wound

Starting at 13th level, the first successful melee weapon attack against a target causes an internal wound.
The target takes your Dexterity modifier as Necrotic Damage at the start of each of its turns.
Unless the target is healed or cured (whether it be magically or medically), the effect persists.

Unknown Entity

Upon reaching 17th level, when an allied creature successfully attacks another creature within 5ft of you, you may attack that target aswell.
The target does not realize it has been struck by you.
This does not count as a reaction, but you may only do this once per turn and can only target the same creature once every minute.