I would die laughing if she approached him for business. Because he would be so utterly confused for several minutes. He'd get it, but it'd take a minute.

And the lower districts would be awesome. He's going to be working down there. If he goes down there during the day, he's taking notes and writing out plans and looks educated/well-off.

And either pickpocketing - which would make him feel sorry for her - or business - again, he'd worry about her - would be awesome.