The homeless population consists largely of people with criminal histories, psychiatric problems and/or addiction issues.
According to the Substance Abuse and Mental Health Services Administration, 20 to 25% of the homeless population in the United States suffers from some form of severe mental illness. Even mild mental illness can make it impossible for person to hold a job or deal with society.
"Starting in the 1960s, there has been a worldwide trend toward moving psychiatric patients from hospital settings to less restricting settings in the community, a shift known as "deinstitutionalization". Because the shift was typically not accompanied by a commensurate development of community-based services, critics say that deinstitutionalization has led to large numbers of people who would once have been inpatients as instead being incarcerated or becoming homeless."
[The] risk of homelessness increases for people with multiple convictions. The Prison Policy Initiative found that people who have been incarcerated more than once are 13 times more likely than the general public to experience homelessness, whereas people who have been incarcerated once are 7 times more likely.
The National Coalition for the Homeless has found that 38% of homeless people are alcohol dependent, and 26% are dependent on other harmful chemicals. I suspect that there are more abusable drugs today than in the past. It's not too difficult for prospective landlords and employers to recognize a pockmarked methamphetamine addict for example.
Years ago, a person could escape their past (criminal and otherwise) by simply moving to another part of the country and re-inventing themselves. It was relatively easy for a person to assume a new name and identity. Not that was necessary. Simply relocating was enough to get fresh start.
Until relatively recently the police didn't have access to a database to check a person's criminal history, much less employers and landlords. Stories about people escaping their wayward pasts was a common theme in old movies. Nowadays if you have criminal record it follows you wherever you go. Employers, landlords and anybody else can simply Google your name to know if you have a prison record. The information age makes it very hard to escape the stigma of unsavory past.
The combination of ex-felons, addicts and people with psychiatric problems found in homeless camps is a toxic brew that makes life difficult for any homeless person and another obstacle in their efforts to escape homelessness.