He also oversaw a doubling of the prison population during his presidency. That’s not entirely (and maybe not even mostly) his fault - Congress and plenty of states were all about being “tough on crime,” but he was definitely on board with it. That probably also contributed to homelessness. People are significantly more likely than the general population to be homeless post-incarceration, and anyone who’s done time can tell you that it makes a lot harder to get a good job.