You are not one to do the dirty work, your involvement often encompasses giving others that work to do. But you've spent much time steeped shoulder-deep in villainy and you're not one to be underestimated in these matters. While not favouring a hands-on approach, you know how to maximise profits, give matters the sometimes necessary push and coax others into doing precisely what is needed, all while remaining perfectly innocent in the perception of law-abiding citizens around you.

Marks of Affiliation

Starting at 3rd level, you gain access to a unanimous sign of your criminal connections, evident to those in the know while only mildly jarring to the uninitiated, which you can display to identify your more unsavoury side or flaunt such connections. This can be an item you previously owned or a new possession, usually a piece of jewellery (such as a signet ring). You're also privy to certain lawless secrets that you can use to verbally communicate your alignments.

You can flaunt either article in combat using a bonus action. Possible reactions to them can be a gamble, but their general nature suggests you're not a novice. As such, it might have logically more favourable results on lowly cutpurses than on veteran guardians of the Law.

Respectable Front

Many criminals choose to live in the uncertainty of always fleeing newer and newer forces of Law. Some see respite among the wretched and the shrouded. You, however, whether by luck or tremendous preparations, carved out a legitimate operation that gives credence to your false claims and obfuscates your otherwise obvious crimes. This false Respectable Front can take on many forms: a genuine business, engrossing political activism, a streak of investment-heavy academic expeditions. Whatever its shape, that's the mask you present to those who shouldn't know about your more illicit activities.

While playing out your Front, you can change Deception rolls that you'd normally need to take to rolls of other Charisma-derived skills, with your DM's permission.

Beyond that, your Front can serve as a minor aide to your schemes, too. Being a more-or-less legitimate piece of work, it gives you access to resources you can use back in your criminal endeavours. This help is the Methods of your Respectable Front. Those Methods will give you a small bonus when playing out your Front. One now and one more at 17th level, alongside the Centre of the Web feature.

Manipulation

You know how to grease the wheels properly and have people around you do precisely what is required. You can generally wave off disadvantages in social interactions or create advantages by offering adequate incentives, whether material or not. Through promises of items, titles, money and the like you can gain advantage or lose disadvantage on rolls for Charisma-derived skills, assuming the incentive is deemed apt by the DM.

Of course, if it turns out you don't actually have the promised resources, the situation might get sour if you meet the bribed person again.

Observation

Action is what gets one in trouble. Sometimes it's better to be wary rather than rash. You use the safety of your Respectable Front to take a closer look at people, their routines and their houses. You can choose one skill, Investigation, Perception or Insight, to become proficient in when anyone interacting with you is convinced of your Front and none of your criminal affiliations shows.

You can change the chosen skill after completing a short or a long rest. If you're already proficient in it, no bonus is applied.

Subversion

People are an epiphenomenon. You know it's about the shape of the board rather than the pieces. You gain proficiency with a forgery kit and one more professional tool set.

Affluent Aura

Starting at 9th level, you know how to project the necessary air of respectability around you and use your mere presence as a cunning weapon. When out of combat, you can choose to unleash this Affluent Aura, prompting everyone in 45 feet radius around you to roll a DC 15 Wisdom save. Those who fail fall under your aura's spell.

The Aura's effect ends after 1 hour, exploiting it 3 times, doing something that strongly goes against your visage as shown by your chosen options or when otherwise specified by certain options. Once used, you can only use the Aura again after a short or a long rest.

You can choose one effect your aura has on affected targets now, and a second effect at 13th level.

Devastating Snub

Your opinion of others means a lot. Especially when it's negative. As little as a snark remark, or even the force of being ignored by you, is enough to devastate some. You can choose a creature affected by your Affluent Aura to deal [roll]2d6[/roll] + your Charisma modifier Psychic damage to them.

You can can't use this twice on the same creature during one Aura. Doing this twice ends your Affluent Aura instantaneously.

Enchanting Presence

Creatures under your Affluent Aura's sway are enamoured with your sheer presence, believing and nodding to everything you might say. You gain advantage on Persuasion, Deception and Performance rolls against them.

Imposing Airs

Something about you dominates the room in a somewhat suspenseful, perhaps even dreadful manner. You have the air making to that of a seasoned law-hound or a grizzled military officer about you, coercing others into treating you with the necessary respect and submission. You gain advantage on Intimidation rolls against creatures affected by your Affluent Aura. Furthermore, these creatures will not start combat by engaging with you while within the Aura's range.

Starstruck Awe

Some people have a way of attracting everyone's attention in a flicker of a second. Some people include you. While your Affluent Aura is active, you can choose to activate Starstruck Awe by doing something especially flashy or distinct - this can range from snapping your fingers or clearing your throat to reciting a characteristic phrase - causing everyone under your Aura's influence to stop what they are doing for one turn and look at you, whether their gaze will linger with interest or not. Creatures that are especially familiar with your antics (including, primarily, your party) are unaffected by this.

If a creature affected by your Aura lacks the sense(s) necessary to perceive your attention cue, they're unaffected by it.

Once used, your Affluent Aura dissipates instantaneously.

Practical Lessons

By 13th level, you have spent enough time with more field-active rogues to pick up the basics of their job and how to mimic the professionalism of one other roguish archetype. You gain the bonuses of a different archetype's first, "basic" feature.

Assassinate

You are at your deadliest when you get the drop on your enemies. You have advantage on attack rolls against any creature that hasn't taken a turn in the combat yet. In addition, any hit you score against a creature that is surprised is a critical hit.

Fast Hands

You can use the bonus action granted by your Cunning Action to make a Dexterity (Sleight of Hand) check, use your thieves’ tools to disarm a trap or open a lock, or take the Use an Object action.

Insightful Fighting

You gain the ability to decipher an opponent's tactics and develop a counter to them. As a bonus action, you make a Wisdom (Insight) check against a creature you can see that isn't incapacitated, contested by the target's Charisma (Deception) check. If you succeed, you can use your Sneak Attack against that target even if you don't have advantage on the attack roll, but not if you have disadvantage on it.

This benefit lasts for 1 minute or until you successfully use this feature against a different target.

Master of Intrigue

You gain proficiency with the disguise kit, the forgery kit, and one gaming set of your choice. You also learn two languages of your choice.

Additionally, you can unerringly mimic the speech patterns and accent of a creature that you hear speak for at least 1 minute, enabling you to pass yourself off as a native speaker of a particular land, provided that you know the language.

Psychic Blades

You can manifest your (newfound) psionic power as shimmering blades of psychic energy. Whenever you take the Attack action, you can manifest a psychic blade from your free hand and make the attack with that blade. This magic blade is a simple melee weapon with the finesse and thrown properties. It has a normal range of 60 feet and no long range, and on a hit, it deals psychic damage equal to 1d6 plus the ability modifier you used for the attack roll. The blade vanishes immediately after it hits or misses its target, and it leaves no mark on its target if it deals damage.

After you attack with the blade, you can make a melee or ranged weapon attack with a second psychic blade as a bonus action on the same turn, provided your other hand is free to create it. The damage die of this bonus attack is 1d4, instead of 1d6.

 

Rakish Audacity

Your confidence propels you into battle. You can give yourself a bonus to your initiative rolls equal to your Charisma modifier.

You also gain an additional way to use your Sneak Attack; you don't need advantage on the attack roll to use your Sneak Attack against a creature if you are within 5 feet of it, no other creatures are within 5 feet of you, and you don't have disadvantage on the attack roll. All the other rules for Sneak Attack still apply to you.

Survivalist

You gain proficiency in the Nature and Survival 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.

Whispers of the Dead

Echoes of those who have died cling to you. Whenever you finish a short or long rest, you can gain one skill or tool proficiency of your choice, as a ghostly presence shares its knowledge with you. You lose this proficiency when you use this feature to choose a different proficiency that you lack.

Centre of the Web

When you reach 17th level, you have learnt the ins and outs of criminal trades thoroughly and profoundly. You can easily discern a criminal from a crowd after observing or interacting with them for at least a minute and any such criminal impediments known to you suffer disadvantage to their skill rolls against you.

Furthermore, when engrossed in playing out your Respectable Front, you gain an additional bonus based on your Front's Methods:

• Observation - If you're already proficient in the skill you chose to become temporarily proficient in, its passive version is increased by 2 instead.
• Manipulation - Once every short rest, when outside of combat and convincingly playing out your Respectable Front, you can charm one person for an hour. To this person, you'll appear as entirely friendly, believable and good-intentioned.
• Subversion - Once every short rest you can surreptitiously disrupt the casting of a Divination spell whose level is your CHA modifier x 2 at most, provided you're within 5 ft range around the caster, thus causing the spell to automatically fail.