I actually like this shot very much. But, the distance from the subject makes it a bit difficult to get a good read on their actual character. Still, great lighting and DOF.

Everything about this is wonderful. Saying that, maybe cropping a little of the left-hand side would give a tighter focus, I don't know.

To me this is more of a street scene than a portrait

I like the despair in this image, but I'm distracted by the composition

The background feels a little cluttered & distracts from the main subject a little, though you have captured something in your subject which makes the viewer consider their circumstances.