Visited Portlandia about ten years ago (caught a city-wide music festival by accident too) and was astounded by the volume and brazenness of the "homeless" people there (who drive nicer cars than I do).
Now, it seems to be a booming industry. Nearly every intersection here in CT is adorned with one or more people looking for handouts.
My latest business scheme is to make quality beggar signs for these people. Completely weather-proof, but looking like used scraps of cardboard, lettered via sharpie, by trained fourth-graders, for an authentic look and feel. For slightly more, I'll professionally apply Taco Bell sauce in strategic locations to really put it over the top (ask for the premium package!).