Criminal Accountant

"He who holds the purse strings, rules the house, the nation, the world. "

Not every criminal organization is run by assassination and violence. Some are run by very cunningly controlling the root of all evil: money. That's where the Accountant comes in.

Their position might not sound like the most interesting in the world, and that's exactly how they like it. These are not the faces of the criminal syndicate. Instead, they keep to the shadows, trying to be as unobtrusive as possible. They live to be underestimated, but at the end of the day, they hold all the cards.

Their business is to know. They know how much money is coming in and out, what goods are going where, which politicians are being bribed, and where the contraband can be found. They balance the books... or unbalance, as the case may be -- by shaving a little off the top, they're assured that, good or bad, they always profit.

War is good for business.
Peace is good for business.

A Little Off the Top

You know right where to go to find what you want... but you're not the most willing to share. When you take this archetype at 3rd level, you gain advantage on all Intelligence (Investigation) checks while hidden.

Additionally, you know exactly when you're being swindled. You gain advantage on all Wisdom (Insight) checks on friendly creatures when discussing treasure, money, or loot, or when bartering.

A Smuggler's Mind

Your years spent skulking around docks and watching over illegal shipments have granted you certain instincts when it comes to the comings and goings of people and products.

When you choose this archetype at 3rd level, you can add your Intelligence modifier to your roll for any Wisdom (Perception), Charisma (Deception), or Dexterity (Sleight of Hand) check.

Secret Stash

At 9th level, you gain the ability to create a charm that allows you to access a pocket dimension that can hold a number of light weapons, small magical items, or potions equal to your Intelligence modifier + your rogue level. The creation involves a simple arcane ritual costing 25 gold in crafting materials and 1 hour of time. You can remove and use an item from it as part of your Cunning Action, but you need at least one hand free in order to do it.

Your charm shatters when you fall unconscious by any effect other than sleep. If your charm is broken, your connection to the dimension severs and you lose the ability to access contents of the pocket dimension until you are able to perform the ritual again.

Blackmail

At 13th level, you've learned to magically deal in the most valuable commodity: secrets.

As an action, you whisper a phrase to one creature within 5 feet of you. The target must make a Wisdom saving throw against 8 + your proficiency bonus + your Intelligence modifier. It automatically succeeds if it doesn’t share a language with you or if it can’t hear you.

On a successful saving throw, your whisper sounds like unintelligible mumbling and has no effect. If the target fails its saving throw, it is charmed by you for the next 8 hours or until you or your allies attack or damage it.

It interprets the whispers as a description of its most mortifying secret. While you gain no knowledge of this secret, the target is convinced you know it. While charmed in this way, the creature obeys your commands for fear that you will reveal its secret. It won’t risk its life for you or fight for you, unless it was already inclined to do so. It grants you favors and gifts it would offer to a close friend. When the effect ends, the creature has no understanding of why it held you in such fear. Once you use this feature, you can’t use it again until you finish a long rest.

Expert Discerning Eye

When you reach 17th level, your eye for powerful, rare, valuable, and contraband items has no equal.  You can take 10 minutes to examine any item, gaining information about it as though you had cast the identify spell on it, though you do not use magic to do so.  You know the approximate market value of any item you use this feature to examine, regardless of whether it is magical or not.  You can also tell immediately if an item or document is a forgery (no ability check required) provided you have at least some knowledge of what the object is (you can't tell a document written in a language you can't read is a forgery, and you can't tell if a small machine is a fake if you don't know what it does, for example).

Additionally, your study of the value of magical items has given you a deep functional understanding of how they work and how others can use them. You ignore all class, race, and level requirements on the use of magic items. Any time you are attacked by a creature wielding a magical weapon for that attack, you can use your reaction to make an Intelligence Check, contested by the opponent's Charisma (Deception) check. A successful check imposes disadvantage on all attack rolls against you from that weapon for one minute, or until you use this ability on another creature's weapon.