Wish you'd post the whole story in one. Wondering now if it ends well.
We got a homeless tent city in our town between the local dump and the discount food grocery, on what's called 'crown land' (owned by the government) that remains undeveloped. The only way to get there is to hike through a field and brush. About a year ago I provisioned one of their residents, gave her so much stuff she couldn't carry it all on her wagon herself. Imagine a guy in a full suit carrying bags of tarps and food over a three lane road with a little homeless lady and her wagon. Punks tried to run us over. The moment someone thinks you're homeless, you're done (not in the same way you're "done" either). You stop being a person.
The weekly help I gave John made him king of the park so to speak. I did not shower him with money because it takes time to become accustomed to being one of the have after spending time as a have not for so long.
There are slums outside the city that I would not be brave enough to try and enter. I must say that you are a braver person than I am.