It is of course impossible to talk about this subject matter in real terms, based on one's own direct experience, instead of as an abstract theoretical concept, without risking it coming across as a backdoor brag. It's important enough that I'll risk this.

A few things I've noticed and learned:

Homeless people begging on the street for money still ask for "spare change", and in most cases, when someone offers them something, it's exactly that: some change. These days, you need quite a bit of change just to afford something as simple as a black coffee. It seems that the amount that people give to the homeless hasn't kept pace with inflation.

Giving anyone who asks you directly for a few dollars (instead of a few dimes), so that they might get something to eat, hasn't bankrupted me in the last few years. Perhaps if I lived in a larger city, like Los Angeles, then it would. But if I lived in Rome, I'd speak Italian, but that doesn't mean I speak Italian where I live.

There's a clear distinction between people who truly need the money (they tend to be older or mentally unfit) and young people who are backpacking across the country. I'll subsidize helping someone eat when they've been left with no options; I won't subsidize someone who's clearly chosen a nomadic lifestyle.

Onlookers will be critical of you for giving money to beggars. Most of the time, they don't voice their objections to you directly, but then, people usually don't have to say what they're thinking for someone else to hear it. The objections you hear are familiar ones.

Perhaps if a beggar asks me for money, and I give it to him, he takes the money and spends it on alcohol. That's his prerogative, and that's on his conscience, not mine. If a person doesn't know what's best for themselves, then I'm reasonably sure that my single act of refusing to give them anything is not going to teach them a lesson.

I'm not convinced that I've learned what's truly best for myself, and I'm not sure that all purchase decisions I make for myself are things that I should be buying. Case in point: I've spent plenty of money on alcohol in my life. Glass houses...

If I give money to 10 people, and 9 of them spend it on vices that don't help them, but only 1 buys something they truly need, it was worth it for that one. I'm sure the actual ratio is much better than this.

No one likes asking strangers for help; for most people, there's enough shame in having to do this that this is a matter of last resort. I was told in 7th grade by one of my teachers that most homeless people asking for money on the street make a killing collecting money, and at the end of the day, they walk to their Mercedes' and drive home. I've since polled people with nice cars; I've never met one who earns their keep begging. (Though I can't rule out the possibility that some of them exist someplace.)

If I'm walking down the street with leftovers from a restaurant, I've very often been asked by beggars if they can have my leftovers to eat. I never refuse those requests; I'm not sure if the risk of transferring a pathogen is high enough to make this a bad course.

There's an old children's book I used to read called If You Give A Mouse A Cookie, the moral of which is that if you give a person a little, they'll keep asking for more and more, insatiably. Most people that you give to are truly grateful. Only a small handful of them give credence to this lesson espoused in Cookie and pester you for more. Akin the manner in which the homeless choose to spend their money, this is on them, not me, and it's pretty easy for me to say "no" to any follow-up requests.

Perhaps money is better spent by giving it directly to organizations that are designed to support homeless people in a way that is more sustainable. (If you ask anyone who works at one of these organizations, they'll certainly back that up!) It's extremely difficult to generalize about this, but much of the money going to these organizations goes to support administrative costs surrounding the organization and not to the needy. Most of the organizations I've encountered really aren't doing anything to make things sustainable.

It's dubious to claim that money is wasted going directly to a person in need, but wouldn't be wasted going to one of these organizations. I know that not everyone who is in desperate need of help is on the streets asking for it; many are families who, despite living in houses, are in terrible circumstances. So these organizations are extremely necessary, but we shouldn't draw the false dichotomy where giving to people who ask directly is "bad", while giving to organizations is "good".

Whatever money I have isn't mine. Someone gave it to me, and I'm just holding onto it for a while. In one form or another, the wealth will outlive me.

Last week, I forgot to eat one day. At a couple points, I considered going to get something, but the prospect of seeking out food just seemed like a boring thing to do, relative to the other things I had going on in my life on that day. Mild hunger can get painful quickly. They next day, a man in front of a grocery store asked me for something to eat, and I gave him $5. While I was shopping, I saw him in the same store buying food. On my way out of the store, I ran into him again; he looked better. I offered him a bag of mandarins, but he politely turned them down, and thanked me for the meal. I'm not sure how much better $5 could've been spent by me on anything else.