Help find a happy ending for this story

Story:
I have a co-activist friend in our local liberal group, let's call him, "Arkansas Joe". He is 62, very non-conformist, in relatively good health (though I'm certain he has not had a screening for years or decades - certainly not a dental one), and was very active nationally in the civil rights movement. He has had at least some college education and has been guest speaker at colleges and organizations 'back in the day' (1960s-70s). He is a bit odd and very set in his way of being, but unfortunately quite transient in his 'golden years'. He is not a substance abuser. He is in a constant struggle to survive. He is always on the verge of being evicted due to late rent, having his heat turned off, and getting enough food. His recent source of income has been substitute teaching and he has not been getting calls for that. I suspect it is in part due to his appearance and tendency to be stuck in old teaching ways.

I feel for the guy. I respect him for his service to the progressive movement and also wonder how he can get out of his situation. I told this story to my extremely religious sister-in-law, explaining my struggle to assist him in various ways, and she comes back with a ' teach a man to fish..' type thing. Part of me agrees with her in that he simply has to move with the times if he wants to make a wage, another part of me feels that he has paid his dues and aren't you allowed to be a bit more stubborn and crotchety as you age? Is our society one that simply can't be bothered with guys like this freezing to death? Should I just try to gussy him up and send him to a temp agency to learn Excel?

He has no family to speak of and says they rejected him way back when. He has been illegally held, jailed, beat up, picked on and everything else by 'normal society' and then again by some in the 'liberal/progressive' movement.

Where does he fit in an ideal Progressive world? Where does he fit now? How can you make his case? either an empathetic one to a 3rd party or to him to try and get him to conform enough to have an easier (safer) life. I can donate food and clothes sometimes, but have little money to help. He has recently said, 'I've asked for help, what else can I do?'.