The amount of "bums" or "homeless" people that aren't actually homeless but everyday citizens who can make good, tax-free money by wearing trashy clothes and writing on cardboard is on the rise.
There was a video of a "homeless" man in Texas that could pull at least 60k a year. A good year over 100k.
Family friend was once approached by a woman who claimed to have 3 kids and needed money for diapers, clothes, etc. Friend told the woman to stay at this location and she was going to go out and get her some supplies she needed. Friend came back with said supplies and woman was gone. If the woman REALLY needed those supplies to support her family, I doubt she would have bailed.
Also I remember walking by a "homeless" man asking for cash in the Georgetown area in DC. This guy was also playing on his new flip phone (no smart phones at that time except Blackberry's).
I usually take the ignore, don't-look-at approach. If I feel guilty or in a giving mood, I'll walk in the nearest food place and get a meal to-go for the person.