This is Fie, my fourth edition character. The image on the pdf here was a stock image that closest resembled what I had in mind for her, but I never got around to making a more accurate image. She would be closest to my Saints Row character. Of course, she's a changeling, so I'm only talking about her primary identity.
Part 1 - Fie's history
Changelings born to mixed parentage are still 100% changelings. Fie's father was a half-elf merchant who never knew of his wife's true identity. At the end of her pregnancy, she fled, not knowing whether or not the child would be a changeling. It takes 2 years for a changeling baby to be able to hold its form consistently, which is as long as the wife stayed away before returning to her husband claiming kidnapping and rescue.
Years passed without Fie ever realizing she was different from her peers. Her father being an accomplished merchant, she was sent to school (at her mother's protest), where she eventually noticed the changes of puberty in her classmates. In time she began to discover that she quickly gained features she envied or lost features she feared mocked. Upon confronting her parents about this strangeness, her father dismissed it as the natural course of growing up, but her mother came to her later in private to share with her the history and nature of their race. She took the news well, comparable to Harry being told he was a wizard for the first time. Following that, her very below average grades began to rise steadily as she discovered ways to circumvent the system by way of her ability. Her favorite pursuit, above all else, throughout all of her school career was that of acrobatics - where she excelled naturally.
By graduation, her father had died of age (or something), and she was the top of her class. By this point, she'd developed the sort of arrogant attitude towards the world that says "I'm better than everyone else, I don't need to go about the normal means to do things I want to do." In spite of this attitude, she initially attempted to follow her father's footsteps as an honorable merchant. As soon as she discovered business wasn't so easy, she took to deceit as a means to her wealth and power. Ultimately, she still regards her father as a paragon of business honor, and has vowed to never cheat a man who didn't have it coming. More often than not, however, her influence/temptations of wealth bring out the worst in her targets. At the moment she began to break the law, she created a new identity for herself to protect her late father's reputation. The focus of her "true personality" gradually shifted from her birth face to this newer, harsher visage. Meanwhile, she kept up the appearance her place in her class implied whenever family duties drew her back. (Her primary appearance is human. Her mother's disguise was human as well. She likes to emphasize half-elf features such as high cheek bones and an ever-so-slight point to the ear out of respect to her father).
Part 2 - Her current lifestyle
The bulk of her wealth is from con-games. She enjoys being charitable, perhaps not out of true altruism, but out of the feeling of power that comes from being able to give out money. In the cases that the recipients of her charity are truly in need and use their gifts well, they receive protection and additional support, provided they remain open as contacts/potential participants in cons. In the cases that the gifts are squandered, abused, or otherwise received improperly... shit goes down. For these situations, she keeps the company of a "gang," or at least a group of people who have sworn loyalty to her. As employees, they receive a small stipend for their daily businesses, but are left largely independent. They are under strict instructions to avoid the attention of law enforcement, and thus should never raise hell where hell does not deserve to be. By this axiom, they are viewed by the communities they inhabit as a generally positive presence. They keep away a worse element of criminal activity and discourage assholery in the neighborhood.
Gang members who betray this expected behavior are dealt with mercilessly.
As a con artist, Fie is known by her gang to travel a lot. Her quest for additional control is not limited to her home city, though, as she's held ambitions to expand into other towns for some time. Some of her identities have become known for their bravery in neighboring regions. She sometimes acts as gang leader to bolster her own personal reputation, but more often than not, she acts in the guise of a follower to prove the power and reach of the organization, plus the effectiveness of its leadership.
Within any given con game, she pays her accomplices well, but tends to minimize their number by playing most roles of the con herself. Nobody within her organization knows her race. They assume each of her identities is just another member, or in some cases, some another leader.
All of her criminal activity is governed by reason primarily. If there's no gain in an act, she will not do it. If being cruel doesn't make sense, she won't be cruel. If she needs to be a little mean to get something done, she's not afraid to do that either. She also will never hire someone for a job she can do herself. More often than not, the problem she runs into is a lack of additional hands.
Part 3: The faces of Fie
These are some of her personas which she's spent time developing and building reputations for.
Smidduck the dwarf archer - stocky, deep-voiced, smallbraids throughout his long beard. Broken nose and square features.
Johan the plucky thief - Norwegian features, blonde hair, light eyebrows, strong jaw. (human)
Elric Percival Longbottom the diplomant - an identity complete with nobility papers (acquired through the con of a noble family, claiming heritage as a cousin, and gaining access to the family's name by promising not to partake of its wealth). This guy is very proper, wears very expensive clothes, speaks articulately. She uses this face for situations where she needs to impress a politician. (human)
Swig the thug - rough around the edges, very interested in bashing skulls. Tall, brawny, imposing - used to scare people who really need to see size to feel fear. (goliath)
Walt Brimley - very fat old man with a mustache. Kind, jovial, helpful, surprisingly politically conservative and tends to make people uncomfortable with his opinions. (human)
She has clothes and equipment in her handy haversack for each of these identities. Each set of equipment is contained in another sack she can take out and use to conceal her own bag. Another extra bag contains a random assortment of clothes for impromptu identities.
Some of these people are introduced as members of the gang prior to her departure ("I'm going to go get my muscle guy, brb"), but when she's confronted about the oddity of her never being in the same room, she'd say "We limit the amount of time we're seen together to avoid recognition as a group. It's easier to notice a group than an individual."