Expert

Whereas other roguish archetypes fixate upon a single larcenous calling, the Expert's wide range of skills are most often the accidental byproduct of a desperate mercenary lifestyle; years of saying yes to every paying client has forced you to try your hand at every kind of job at least once, from assassination to rat catching to book keeping, and taught you the value of audacious self reliance when operating far outside of your comfort zone. Experts pair that confidence with a quick wit that learns best on the job, granting them a wide range of practical skills that get even sharper under stress.

Roguish Audacity

Starting at 3rd level, your wide range of skills begin to prove their worth. Any time that you succeed on a skill check that you are proficient in, you gain Heroic Inspiration. In addition, when rolling a skill check that you are proficient in, you may spend Heroic Inspiration to roll with Advantage and add double your proficiency bonus to that roll, as if you had Expertise in that skill. If you already have Expertise in that skill, then using Heroic Inspiration only adds Advantage to the roll.

Bonus Proficiencies

Also at 3rd level, you gain proficiency with any three skills of your choice.

Ace of Trades

At 9th level, your experience in various trade skills broadens your worldly repertoire. You apply double your proficiency bonus to rolls that utilize tools or vehicles that you are proficient in.

In addition, you gain proficiency with any four tools or vehicles of your choice.

Voice of Experience

At 13th level, your pithy advice effectively conveys your years of experience to others. As a bonus action on your turn, you may use your Cunning Action to grant another creature within 30 feet your proficiency bonus for a single skill or tool for 10 minutes, so long as that creature can hear you and understands the language you are speaking. If you have expertise in that skill or tool, then the creature applies double your proficiency bonus, instead.

This feature cannot be used to lower a creature's proficiency bonus if it would be higher than your own.

Master of All

Starting at level 17, you know everything that is worth knowing about living. You become proficient in every skill.