You say it as though it were a bad thing. He has money coming in, has a roof over his head, does fulfilling work, and from his description is quite satisfied with his life. Where is the problem?

It means that he needs help, even if he doesn't need offers of help, even if he doesn't need more help.

I didn't think I put a negative spin on it. I was responding to the other person's rant about 'collectivists'.

The problem is we can't all do that.

I'd love to have all that and not need to work. I also do fulfilling work for myself and so I meet all the requirements. How can I sign up to that gravy train?

I didn't know that. I'd argue that those more local to him would be in a better position to help him than the collective, which needs to pool money from all its constituents, give it to bureaucrats who take their share of it, in order to eventually make a check arrive at his inbox.

So if we really care for him, it should be eye-opening how those good intentions turned into "Everyone! Give one cent to this politician (or you'll be jailed) so he can eventually make some of this money arrive to the person that needs help". How about those around him help him? Churches want to help but current policies curb them (cue the recent 90-year old that was arrested for feeding the homeless).

Those policies aren't there to enforce some kind of state monopoly on the distribution of aid, they're there because rich people don't want to be reminded homeless people exist.