Not sure what the mask is doing here but, maybe to keep warm?
Street photography is just talking to people...you wouldn't hesitate to ask a stranger the time or when the bus comes. No different to me. In this case, I got to know this kid over the past 6 months or so, talking as I pass by or tossing him a few bucks as he played. He's quite an interesting character, convinced he's a genius, actually.
@Colin Corneau interesting insight . . . I live in a very rural are . . so street photography . . . do my neighbors count? Is that a Camera Repair shop across the street??
I spent many years in a rural small city. Really got my start in street photography there as watching for details and going for walks helped keep me from going stir crazy from boredom.
It is indeed a camera repair place and a damn fine one, too! They just posted something today about repairing some gear for the camera crew working with John Cleese, who's in town for an appearance!