Musings from worldwide observations

I'm on a mental journey again, pondering something on which I hope to gain more wisdom- from somebody, anybody. When I went to Hawaii I was impressed by the number of homeless (mostly men) there. They weren't begging. They just seemed to want to live free and easy. I have always remembered an interview on a television program of a homeless man who said that he preferred not having to be tied down to a job and rent or mortgage. In Jordan and Israel I saw lots of Bedouin dwellings which could probably be likened to American Indian tepees. They live a nomadic lifestyle mostly, although maybe not as much as several generations ago. I have noticed comments about poverty and freedom to choose and lack of opportunity on social media. I have been trying to figure out what's fair and how to achieve it.
I have read lots of Benjamin Franklin and he made note of the Indian's disinterest in living a settled, ambitious life. I have heard (and even expressed it myself) sentiments of admiration for the relaxed lifestyle lived on Polynesian islands. Yet, living hand-to-mouth and just surviving is generally considered undesirable. It is considered "advanced" for a civilization to go from mere struggling for food and shelter to philosophy and fine art. Then there are scriptures like, "Succor those that stand in need of your succor; ye will administer of your substance unto him that standeth in need.." But also, "The idle shall not eat the bread of the laborer.,"
How do we know when what looks like poverty is a choice- either because someone prefers to be whatever you want to call it: lazy, carefree, having a simpler life, not tied down by material things, or maybe mental or health issues like addictions (you can't force anyone to give up an addiction- you can help them but only after they have decided they want help) or schizophrenia (they used to force people into lifelong institutions but have decided that's inhumane so often those people are on the streets often not taking prescribed medications that could help)?? Do you hand a homeless person at an intersection a candy bar out of your car window or put money into a Salvation Army bucket and call that good? Do you simply smile at a homeless person in a park, treating them like a "regular" person, and go on your way unless he/she actually asks for something? If you are approached by a beggar with a smartphone and you don't have one because you haven't felt like you could afford it, do you give money to them? When is it an insult to "help" someone who wants to live the way they are and isn't interested in changing? When is it an insult to pity someone who may be choosing to have "less" than they could have? How much is enough- a sandwich a day? 3 full meals? A house? A cardboard box? What if there are children and they would like a better life but their parent(s) is a druggy but has legal custody and doesn't want "help"?
Not only this, but I have learned that babies don't learn to walk if you never let them try, even if they stumble and do it poorly. On the other hand, lack of nurture and attention to babies stunts them for life. Older people move slowly but if you do everything for them then they don't move at all and soon lose the capability to move, even if they wanted to. Helping is not always helpful. I have tended to try to offer or even just help without being asked because I always thought it was the most thoughtful way. Sometimes people claim they don't need help because they just don't want to be a bother. How do you judge?
I realize these are all vague "what-if" kinds of questions. My heart is always drawn out to anyone who lacks things that I might be able to provide. However, I also (like Benjamin Franklin) dislike those who would choose to be indolent but would love to take whatever you would give them or do for them that they could do for themselves but choose not to. Do I walk around with blinders on so I don't feel bad for anyone in need until they are right in my face? Do I not assist until someone falls to the floor in front of me?
I sure feel like I lack the wisdom to be like Jesus Christ even a little bit. As in so many things, you can automatically eliminate the extremes of the spectrum. Truth always lies somewhere in the middle but it's so hard to figure out where to draw the line.