One difficult thing I've had to learn is that you really need to probe for people's committedness/alignment. There are billions of needy cases in the world, and if you don't carefully pick and choose, a steady stream of them that you come across will deplete you of resources and energy, and then you'll have had time gone by with nothing to show for it. Merely pitching in for people, instead of having a clear framework for how they can get in charge of their lives, will only exhaust you. You can orient yourself towards being detachable from most of the capitalist nexus with the ability to onboard committed people to do the same, or you can be a charity, taking care of people's daily and monthly needs.
In the past 4 years I've lent out almost $10k, and covered another $6k in rent for friends that I invited to live with me to save them from being homeless. I'm optimistically going to get maybe a quarter of all that back over the next 2-3 years. It probably would have made everyone better off if I wrote out a contract, obliging people to make a budget and follow it: if I can live on $400 a month, they should be able to live on $800 a month.
Specifically, I wonder whether I would have been able to make a down payment on a house with all that money, and then be able to more cheaply and easily and permanently harbor even more people. Everything you spend playing defense is something you can't spend playing offense.
In terms of energy and motivation, it takes a leap to get to a self-supporting position, but it's super easy to do something if another person is literally volunteering to do all the executive function for you. If someone can't even tack on to something happening right in front of them that they're invited to, they're only going to be dead weight for the foreseeable future. I've been the one in the position of being broke and crashing with friends for extended periods before I finally got over myself and accepted the mediocre jobs that were in arm's reach, but I at least did a couple chores here and there. I guess you either learn something from the experience or you don't.