Thing is, we met him before in Spielburg (in QfG1). As he says in QfG5 (if you tell him about yourself):"Adventurers think they can fight monsters forever. Next thing they know, they are begging in alleyways. A sad fate for a once respectable Hero. So save today to keep the alleys away, I always say."
So he should know all there is to know about begging. But now I wonder: maybe Sam was an adventurer before he became a beggar. So he'd be talking from experience. What do you think?"I thought you lookd familiar. Yeah, we met in Spielburg where I was working the alley as a professional panhandler."
From adventurer to beggar to banker, he's still getting other people to give him money!