Take it with a grain of salt as I'm not very used to 5e. But mechanically which do you feel would fit better/supply the skills you're missing? Example being I took urchin over criminal myself in part because the supplied skills better fit what I planned with the character.<br/><br/>Flavour wise which do you see her relying more in her past? Did she use cons and tricks to slip in close to her targets or more sneaking in the dark and knifing them as they slept?<br/><br/>Also depending on your reason/GM allowance you can swap the bonus ability the backgrounds give. Got an urchin with criminal contacts instead of knowledge of the streets due to that. :)<br/><br/>Will admit given the small town/kinda backwards but progressing vibe I get from the setting I'd think charlatan would fit more. <.<  >.> Unless your character is one that's recently arrived to town?