Thank you. The pull request was a big moment for me.
When I was homeless, random acts of kindness were a godsend and I generally preferred cash, but sometimes a jacket or blanket in cold weather was hugely helpful and even better than cash at that moment. Occasionally, someone gifted me a hotel stay and it made a big difference.
I wrote some about those ideas here:
http://whathelpsthehomeless.blogspot.com/2015/01/random-acts...
http://whathelpsthehomeless.blogspot.com/2017/02/cash-and-gi...
http://whathelpsthehomeless.blogspot.com/2016/12/hotel-stays...
http://whathelpsthehomeless.blogspot.com/2016/11/free-clean-...
To be clear, I never begged or made up stories about having lost my but ticket or whatever. People just sometimes identified me as homeless and did things like offered to pay my grocery tab as I was checking out or handed me a gift card or handed me a blanket. I think you would maybe need to think a bit about how to spot homeless people in situations where it would make sense to do that sort of thing to feel confident this isn't some con game.
One of the problems with "trying to help the homeless" is the Shirky Principle: "Organizations will tend to preserve the problem to which they are the solution." If you really want to see fewer homeless people on the street, it's best to work to find ways to prevent homelessness and reduce the incidence of it as opposed to focusing solely on helping those already out in the street.
Yes, people who are currently out in the street desperately need some help. But the one thing I most wanted help with while homeless was help trying to establish an earned income so I could get my life back and almost no one took me seriously on that point. I was viewed as a "charity case" and no one anyone would want to pay for services.
Someone on Metafilter once characterized my efforts to monetize my websites as me "panhandling the internet." Meanwhile, Metafilter brags about providing well-paid cushy work for it's paid moderating staff and takes donations for their site since their ad money was infamously cut by some change in the Adsense algorithm. But me taking donations for my writing was somehow "different" from what they were doing and "bad."
I've run into similar issues since getting off the street. For a time, I did volunteer work for local charities that nominally do economic development. I quit all my volunteer work back in May of this year. They wouldn't help me establish a better income and didn't really want to pay me (even when there was a payment agreement, they made me feel like I was misbehaving to expect my check in a timely fashion), while eager to give me more unpaid volunteer work because I was getting things done.
It's an insidious form of classism that says "We like what you do, but we don't think you deserve to be paid because you are too poor to dress right" or something. It's a trap that's shockingly hard to escape: I'm too poor for anyone to think I deserve a middle class wage for my work, even if I am doing good quality work, so I can't get rich enough to dress well enough to signal socially that I deserve a middle class wage for my work. People want more of that work from me but they want it for free on the justification that I don't dress right or some nonsense.
In the US, I would like to see universal health care coverage and I would like to see changes to our housing policies. There is a shocking shortage of "affordable housing" -- unfortunately, that's a really loaded term. It means a particular thing to most people. I mean it as literally as possible, but it is perhaps best to describe what I mean and that is smaller homes in walkable neighborhoods available at a modest price even though it is market rate housing and not some kind of homeless program.
A lot of people on the street have some income, just not enough to support a middle class lifestyle. Cost of housing and inability to find inexpensive housing that supports a car-free lifestyle are two big challenges in the US for the sorts of people who end up on the street.
I would be all for someone starting a business that builds Missing Middle housing as a for profit endeavor or that builds SROs as a for profit endeavor. In many places in the US, we have thrown up zoning barriers to building Missing Middle housing and we have torn down a million SROs in the US in recent decades. SROs used to be normal market-rate housing for ordinary people with ordinary jobs who just wanted to rent a room. Now, we think of them solely as part of some homeless program to help people get off the street, and that means that ordinary people with not much money get forced into being "charity cases" instead of having humble but independent lives.
https://en.wikipedia.org/wiki/Single_room_occupancy
I think if you want to be helpful in this space, it's useful to keep two things in mind:
1. On an individual basis: The sorts of problems that lead to homelessness can be hard to remedy, so even if they are making a sincere effort, it can take a long time to see results. (So don't expect a one-time gift of cash or something to magically remedy their situation.)
2. On a societal level: In a perfect world, we would do a better job of caring for "the people" such that having some kind of personal issue would be less likely to cause your life to come unraveled and land you on the street. That means doing a better job addressing basic needs like health care, housing, transportation even if someone can't drive for some reason and so forth and doing so simply because people exist and not based on them finally being desperate enough to qualify for some needs-based program or other.