How old do people in this world live? 28 just seems a little long in the tooth for an amateur rogue with little pick pocketing experience to get sponsorship in a guild. You wouldn't really be suited to working a market, and be a little old for B&E training. Coming from a small village I doubt you've much experience running the thieves highway for example. If the town was large enough you might be able to put feminine charms to work wooing young, gullible merchants to private interludes and stealing their clobber but you wouldn't be able to work that scheme for very long in one place. It would probably be easier to collect information for the guild, set yourself up as a local constable's regular bit on the side or as a serving girl in an important household. What sort of merchant was Pappa? Your talent may lie in the seedier side of that field, arid regions tend to be big on gems. If he was a wine merchant your own knowledge of it could help when masquerading as someone of a higher class.
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