When traveling, I met many who lived by the mantra of self-sufficiency. It seemed both to liberate and consume them.

Daily now I see people living on the street with a lot more, but still with needs of all sorts.

In some schools of Buddhism, the tradition was to live with only one bowl and one spoon. The practice was to beg daily - yes, for food, but mainly to submit to the judgment of society as to whether one's practice is worth it to others. The premise was that people would give if they see you as worthy, not because they pity you.

I would ask the OP to reflect publicly on what he discovered about his own attachments, sense of place, and relations with others and himself. That could be helpful even to people in more tangled circumstance.