Everything you just described as wanting in your background, except the insight skill, is the charlatan. Insight you get either by taking it as a rogue or half-elf skill or taking sleight of hand as one of those skills, opening up the charlatan slot.<br/><br/>Would you're character have broken ties with her handlers? As I haven't built a secretive order of assassins with the resources or bent to break/induct children for Pharse, we might have to work on them if you expect them to be a thing in play. Or it could just be one, semi-retired assassin testing a theory. Post here or PM me about it.<br/><br/>(A courtesan is a high class prostitute catering to the court. A courtier is a, likely non-noble, player in the court. A female courtier is a courtier.)<br/><br/>Bibliophilia, no worries.