Guttersnipe

Be they brutish thugs and enforcers, swift urchins and couriers, or efficient assassins and bounty hunters, guttersnipes never fight fair. Keen on jumping onto weak targets and locking them down with grapples, trips, and dirty strikes, the Guttersnipe excels at disabling lone targets and dragging enemies away from their allies to make quick work of them. Guttersnipes are a moderately successful duelists and can usually hold their own in a straight fight, but they shine brightest when paired with allies who can give them openings on weaker targets and keep said target's friends from interfering with the guttersnipe's brutal ministrations. Unlike many other rogues, guttersnipes tend to favor the front lines and close melee skirmishing as opposed to ranged combat, and as a result are usually hardier folk. As the name implies, guttersnipes are city rats through and through, and as such they are knowledgeable on matters of how to navigate through them.

Roughhouser

When you choose this archetype at 3rd level, you can use any weapon you are proficient in to trigger Sneak Attack as long as it lacks the heavy, special, or two-handed property. You can use your Sneak Attack with a versatile weapon, but not while using it with two hands to make the attack.

Additionally, you may grapple or shove an opponent as a bonus action.

Dirty Tricks

Starting at 3rd level, you have learned a number of ways to distract and disable your enemies. You can make an unarmed strike attack as an action against a creature up to one size larger than you targeting either the throat and head or groin and legs, forcing the target creature to make a Constitution saving throw (DC = 8 + Strength modifier + Proficiency Bonus). If the target fails its save, then a blow aimed at the throat or head will force it to lose its action next turn, while a blow aimed at the groin or legs will force it to lose its movement next turn. If the target has another means of moving such as wings or magic, it may still move using that method, though when attacking a creature with wings the wings may be targeted to prevent flight. If you have advantage on the attack, then the target has disadvantage on the save. This attack cannot trigger Sneak Attack.

Urban Navigator

Starting at 9th level, your ability to find your way around urban landscapes is honed to a masterful degree. You gain proficiency in Investigation and have advantage on Athletics checks related to climbing, swimming, and jumping. Given an hour, you can always find any publicly visible structure or establishment within or immediately around a city or appropriately large settlement, and you cannot be lost while within the boundaries of such a settlement.

Additionally, you have a good sense for where the criminal elements of a settlement will congregate, and can always find at least a solid lead on them with a full day's investigation.

Pragmatist

At 13th level, you completely disregard any sense of honor in a fight, and in doing so, may add one of the following modifiers to any use of Dirty Tricks. If Dirty Tricks lands, this modifier will affect the target regardless of whether or not they make their Constitution save. Each modifier may only be applied to a target once in a day. Additionally, any time you grapple, shove, or use Dirty Tricks on an opponent, you can make a free unarmed strike.

Excruciating - The strike is incredibly painful, forcing the target to fail its next saving throw, or giving it disadvantage on its next save if it made the previous Constitution saving throw.

Disarming - The strike targets the nerves in the target's arm or hands,  giving the target disadvantage  on all attacks until the end of its next turn.

Distracting - The strike scatters the target's focus, giving the target disadvantage on all mental checks and saving throws until the end of its next turn, or the beginning of its next turn if it made the saving throw.

Overwhelming - The strike forces the target back 5 ft.

Crippling Offensive

Starting at 17th level, you become an expert at inflicting devastating injuries on the unprepared. When you trigger Sneak Attack on a creature that is surprised, it must make a Constitution saving throw (DC 8 + your Strength modifier + your proficiency bonus). On a failed save, deal a crippling wound to the creature, giving it disadvantage to all checks and saves made using a physical attribute of your choice (Strength, Dexterity, or Constitution).

This wound may be cured either by a long rest, or a casting of Greater Restoration or any healing spell or ability that heals for at least 25 hit points at once.