While it's true that the educated and comfortable aren't really capable of understanding the plight of the poor, they're also in a position to think about these issues in an analytical fashion absent the desperation that comes with poverty. For instance, views on foreign aid to Africa have been changing recently. This is the result of studies that have shown that while well meaning, the aid keeps those receiving it from achieving self sufficiency.
So should we never question the types of aid that we provide in this country? Welfare is both a safety net and a web in from which the poor rarely escape. Are we not creating the same sort of dependence here at home that we do with foreign aid? Is there not a better way for us to be spending that money to help turn these people from perpetually non-productive members of society into contributors? I think we can all agree that our social safety net should act more like a trampoline to help people bottom out and, with a slight jump on their part, return to a height where they can stand on their own two feet.
As such, I think it's our duty as privileged people without the day-to-day concerns of figuring out how to survive to continually question whether the money we're spending to help poor people is being spent in their best interests...albeit with a bit more tact and empathy than GP.