We think in the example you make here the choices karmically are actually somewhat simpler. Most people down on their luck turn to begging as a last resort to sustain their existence and help them in a time of crisis when they might otherwise starve. When people find they can make a living doing this and then choose to simply continue doing it as an occupation because it is simpler and more reliable than finding secure employment somewhere, then they are exploiting the good impulses of a good samaritan under false pretenses by, in effect, becoming a de facto dependent of the commuters. That goes one step beyond being a needy person in a crisis simply needing compassion for a time so they can get back on their feet. If they were to approach those commuters and ask to live in their home and be fed and clothed and housed for free they would almost certainly be resoundly rejected except for unusual circumstances where they had a very compelling story and were truly helpless because of an infirmity, for example, and simply hoping to find someone with a very generous heart who would be willing to take on such a burden. Such things do happen, but that is not the case here. The example proposed is someone who simply finds it easy to beg for money without doing productive work that helps someone else and that is the typical exchange for employment. It is not simply showing up to get a paycheck, it is doing an active process requiring time and energy on someone else’s behalf and receiving compensation financially in return.
So the chronic professional panhandler is essentially creating a lifestyle as a freeloader taking advantage of others. If they are unable to take a regular job because they have emotional problems or other difficulties that will prevent that likelihood, that is a different story. There are people who are ill-equipped to be in the workforce and begging is a last resort. So those individuals have a justification for throwing themselves on the mercy of passersby because they are truly in a wretched existence and have nothing to rely on but the mercy of strangers. A panhandler who has other options in actuality may simply be lazy or more likely does have emotional difficulties making them incompatible in a workplace, so panhandling is the only thing they might be able to manage to keep their independence. Most people seeing the familiar faces of panhandlers will come to feel exploited. That may or may not be justified because of the personal circumstances of the panhandler that are not in evidence. You cannot tell by looking at someone if they are truly unemployable with any degree of certainty. One solution to a potential moral uncertainty here would be to donate once and then let others take their turns.
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