I wrote this "bardic rogue" subclass for the Something Borrowed context a few months ago - I had fun with the concept, but agree with the comments that it needed some fine-tuning. Thought I would post here for more feedback and possible eventual workshopping.

Spoiler: The Virtuoso (contest version)
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Roguish Archetype: The Virtuoso

Whether providing a convenient cover for a heist or simply raising the spirits of the gang back at the hideout, a skilled entertainer can always count on a place in a criminal enterprise. The performing arts, likewise, can be an appealing second career for many criminals seeking to indulge their creative spirits. A connoisseur among con artists, the Virtuoso often fills a support role in fights by distracting enemies and bolstering the spirits of their allies.

Practiced Entertainer
When you choose this archetype at 3rd level, gain proficiency in a musical instrument of your choice and proficiency in Performance if you did not already have it. If you are already Proficient in Performance, gain Expertise in Performance. If you already have Expertise in Performance, gain the Bard feature Song of Rest.

Spoiler: Song of Rest
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Quote Originally Posted by Player's Handbook
...you can use soothing music or oration to help revitalize your wounded allies during a short rest. If you or any friendly creatures who can hear your performance regain hit points at the end of the short rest by spending one or more Hit Dice, each of those creatures regains an extra 1d6 hit points.


Adventurous Accompaniment
The excitement of adventure inspires you, and starting at 3rd level, you are able to share this inspiration via your musical talents, even in the heat of combat. You gain two options for doing so at this level: Bolster and Captivate. A third option, Song of Freedom, becomes available at Level 17.

Using Adventurous Accompaniment provokes Attacks of Opportunity, and cannot be used if you are Deafened. You have a number of uses of this feature equal to your Proficiency bonus and regain them whenever you finish a long rest. Additionally, if initiative is rolled when you have no uses remaining, you regain one use.

Adventurous Accompaniment: Bolster: To bolster allies, choose number of creatures up to your Proficiency bonus (which can include yourself) to be bolstered by your performance. Then, use an action to make a Charisma (Performance) check. Bolstered creatures must be within 60 feet of you and able to hear your performance. Depending on the quality of your performance, a number of effects can occur:

If your Charisma (Performance) check is greater than or equal to...

...5, Bolstered creatures add 1d6 to saving throws.
...10, Bolstered creatures also add 1d6 to skill checks.
...15, Bolstered creatures also add 1d6 to attack rolls.
...20, Bolstered creatures also add 1d6 to damage rolls.

These effects last until the end of your next turn unless you use an action to extend the performance. You may extend the effect for a number of rounds equal to your Charisma bonus (minimum 1) without spending another use of Adventurous Accompaniment.

Adventurous Accompaniment: Captivate: You designate one creature to be captivated by your performance. This creature must be within 30 feet of you, able to see you and able to hear your performance. Use an action to make a Charisma (Performance) check, contested by the creature's Wisdom (Insight) check. If the creature is engaged in combat, your check is made with Disadvantage. If you have personally attacked or otherwise harmed the creature before, your check is made with Disadvantage and the creature's check with Advantage.

These effects last until the end of your next turn unless you use an action to extend the performance. You may extend the effect for a number of rounds equal to your Charisma bonus (minimum 1) without spending another use of Adventurous Accompaniment. You must maintain Concentration for the duration. The effect also ends early if the creature is attacked or takes damage.

Rapid Tempo
Beginning at 9th level, the art of performing in dangerous situations is second nature to you. You can now extend Adventurous Accompaniment Bolster and Captivate effects as bonus actions. However, beginning a performance remains a full-round action.

Battlesong
Starting at 13th level, you can empower your allies' strikes with dramatic musical stings. While an Adventurous Accompaniment effect is active, whenever an ally makes a damage roll, you can use a reaction to add your Sneak Attack damage to the roll if you have not yet used your Sneak Attack this turn (using this feature counts as your use of Sneak Attack for the turn). Your ally must be within 60 feet of you and able to hear you.

Song of Freedom
Starting at 17th level, you have learned a variant of the legendary Song of Freedom and can incorporate its secret chords into your performances. You learn a new way to use Adventurous Accompaniment. Additionally, Adventurous Accompaniment and Battlesong can now affect any creature in range, even if they are Deafened or otherwise unable to hear you.

Adventurous Accompaniment: Song of Freedom
As an action, you can start a performance designed to liberate the afflicted from negative conditions, debilitating curses, and wicked spells. You designate one creature to be affected your performance. Make a Charisma (Performance) check. The quality of your check determines the range of options you have.

If you Performance check is less than 20, nothing extraordinary happens. However, if your Charisma (Performance) check is greater than or equal to...

...20, you may remove one condition of your choice other than Petrified, Blinded, or Deafened. If the condition includes the Incapacitated condition, the Incapacitated condition is also removed. If a creature with 0 Hit Points loses their Unconscious condition, the creature returns to consciousness with 1 hit point.
...25, you also have the option of removing one disease, one curse (including attunement to a cursed item), one level of exhaustion, or a Petrified, Blinded, or Deafened condition.
...30, you can return a dead creature to life if it has been dead for less than 24 hours, did not die of old age, is not undead, and is willing to return to life. The creature returns to life and consciousness with one hit point.

On subsequent rounds, you may extend the performance by using an action to make a new Charisma (Performance) check. You may target the same creature or a different creature in range. You may extend the effect for a number of rounds equal to your Charisma bonus (minimum 1) without spending another use of Adventurous Accompaniment. Once you have performed a Song of Freedom, you may not use this Adventurous Accompaniment option again until you finish a long rest.