While I have empathy for folks who are homeless, I understand there are multiple reasons this happens. Mostly, these folks don't become homeless by accident or through no fault of their own. Insufficient retirement planning is one major reason for Baby Boomers finding themselves living at the poverty level and perhaps unable to afford housing. Another problem is families are for whatever reason less inclined to take care of their own.
Although I am slightly too old to officially be a Baby Boomer. Folks like me who were born between 1922-1945 are referred to as 'the Silent Generation' or 'the Traditionalist generation'. It was commonly understood that children should be seen and not heard. Something my parents did not hesitate to remind me. One thing some of they had in common was that they experienced the Great Depression which was between 1929–1941.
My mom was born in 1923 so she was also part of the Traditionalist generation since there was an overlap. My dad was born in 1916 which is known as 'The Greatest Generation'. Both my parents lived during the Great Depression, which had a big impact on them, although neither parent was ever homeless as they were both children of financially successful professionals.
My paternal grandfather was a dental surgeon, and my maternal grandfather was a Harvard School of Law graduate and corporate attorney with a license to practice in multiple states. Even so, my mom told me of times they had bread and milk for dinner. My paternal grandfather spent a lot of money helping less fortunate family members during that time.
Growing up hearing about the Great Depression was likely instrumental in my being financially conservative most of my adult life. Planning for retirement required my wife and I to make sacrifices along the way. It seems as if many people today have an attitude that they 'deserve' to have everything others do, so they go into debt rather than save for the future. When these folks reach retirement age with no retirement plan or an underfunded one, they sometimes end up impoverished. Like it or not, this is their own doing.