Would you feel that way if this guy was mugging people on the T? Or robbing houses? If he was well dressed and clean cut? I don't see why we should treat a thief any differently because of his appearance or the nature of his theft.

(And as an aside, I have a lot of sympathy for the under-homed, to the point that I give $240/year to the Somerville Homeless Coalition. If this guy were sitting on the corner asking for spare change, I would have no problem with him.)