Lemme learn you a little. With any skill you can get any amount of money within the inventory of the person you are begging. The chances of failure go down with skilling up, but I have not noticed much more success rate. The best place to level this safely is on your local "a boat". The little ones, that you can hop in and drive. They are considered mobs and they will even yell at you when fail. It seems to work identically to pickpocket aside from so far I have never received an item. The most ive gotten was 7pp from a dwarf NPC and I had a skill of 4.
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