Stories like this (video link), about a homeless man who found a large amount of money and returned it to its owner and was subsequently rewarded with a job and some cash, give me conflicted feelings. On the one hand, it's fantastic that the guy could follow through with his conscience to return the money that anyone - homeless or not - would have a hard time turning down, and he deserves some recognition for doing a truly kind thing. On the other hand, there's no reason something extraordinary should be required of someone who's poor for "suburban businessmen" to believe he deserves the means of survival. I can think of a few people whose circumstances of birth have required nothing of them for their survival, let alone extreme comfort.
I don't think that charity in itself is insulting to the recipient. In fact, I think the attitude that accepting financial help is humiliating is a poisonous part of American culture. What I do have a problem with is attaching strings to help, or making poor people jump through hoops so that they can have what many others take for granted.
An acquaintence of mine who'd worked in a homeless shelter was recently telling me about his experience spending the night in a local one, something he'd promised himself he'd do after seeing what he had at his job. He described a sort of militarily-disciplined barracks where the men (homelessness is disproportionately a male problem, btw) were stripped of their possessions and ordered around all day. Apparently it was a very orderly place that was clean and organized. The acquaintence was very impressed by all this, but I was less excited. How could demanding a well-made bed every morning help someone adapt to anything but life in a homeless shelter? Shouldn't the energy spent on clients in a homeless shelter have a larger view than that?
Any individual's situation in poverty - especially homelessness - is extraordinarily complex. If you're homeless, there has to be more than one problem that's contributing to your situation. There is a common problem amongst all the homeless, and all the poor, and that is a lack of money. This can be addressed rather simply. The rest is not so simple, though it is a lot simpler to address problems with substance abuse or get your GED if survival isn't where you spend all of your energy. Adding requirements to money provided - sobriety, religious participation, sterilization - only serves to keep people from addressing the other factors in their own personal situation. And for what? The approval of comfortable people who can't imagine a way to live that is not their own.
Poor people are not pets, they are not dolls, and (surprise surprise) they're human enough to pursue religion or whatever they're interested in. The most effective charities and social programs (housing first, for example) give people the means to pursue something other than surviving while poor, but don't try to re-teach simple lessons about morality that everyone is exposed to.