Since we've basically fully devolved in to politics here, one fundamental stressor I run into in assistance for the poor is that people put as much value on something as it is valuable to them. So free stuff is often treated like trash, even if it should be really valuable. This is a world-wide phenomenon. So means testing, and charging nominal amounts for things is generally a good idea, because people value what they had to invest in. But there is a point at which we shouldn't deny basic human needs to people based on their ability to pay. People shouldn't have to choose between their children's food and their medication, etc. It's problems like that that I find difficult in public policy to help the poor.
So how do we get people adequate housing that they can be proud of without stripping it of its value, and how do we make sure people have food security, and medical security, without devaluing those things? (E.g., going to get a more expensive medical device than required because you know Medicare will pay for it.)
It's one of the reasons I don't like the universal basic income idea, or the free college for all. It shouldn't be free, but it shouldn't be out of reach, either.
And education is a tough part of this. How to deliver quality education to people who aren't food or home secure? Because once people get to the age of majority, if they don't have at least a good base, even trade schools (which should be a bigger deal) are out of reach.
One thing we can do is make sure that people who work full time can afford a basic level of comfort and security.