Info Broker

Knowledge is power, and power is money. Rogues that follow the path of an Info Broker know this better than anyone. Info Brokers have spent their lives perfecting the art of gathering information and finding the value in it. Whether that information comes from their own research, exchanging with others, or more dubious sources, what's important is how you can use it and how much it's worth to the right person. Strengths, weaknesses, tactics, and plans all set Info Brokers apart from any other combatants and traders.

Callous Haggler

When you choose this archetype at 3rd level, you gain proficiency in the Insight and Persuasion skills if you don’t already have it. Your proficiency bonus is doubled for any ability check you make that uses either of those proficiencies.

Accurate Information

When you take this archetype at 3rd level, you know the value that precision holds in both information and combat. When attacking with a weapon that deals piercing damage, you score a critical hit on a roll of 19 or 20.

In addition, weapons that contain both the Finesse and Thrown properties have their base damage increased to 1d6 if it is lower. This bonus increases to 1d8 at 8th level, and 1d10 at 14th level.

Information Exchange

Beginning at 9th level, you have learned to cross communication barriers involving language. You can cast Tongues or Comprehend Languages on yourself a number of times equal to your proficiency bonus per long rest.

In addition, you have advantage on Investigation rolls when searching written information or trying to understand hidden meanings.

Blackmail

Starting at 13th level, you gain the ability gather information in battle and use it to throw your opponent off. As a bonus action, make an Insight check contested by a targets passive Deception. If you succeed, the target has disadvantage on all attack rolls against you for the next minute. If the target isn't intelligent enough to be blackmailed, this ability fails. Once you use this feature, you can’t do so again until you finish a short or long rest.

In addition, you have advantage on Intimidation checks if you have information you can use against the target.

Single Point of Failure

Starting at level 17, you have become adept at analyzing your opponent, taking advantage of any weakness they have, and exploiting their defenses through it. Whenever you score a critical hit, you can choose to lower the Armor Class of the struck enemy by 5 for all allies until the end of your next turn. In addition, the target has disadvantage on all Constitution Saving Throws until the end of your next turn.