My niece has made huge mistakes in her life. I love her dearly, but she was always a difficult child.
A couple of years after she had graduated from high school, she would not look for a job, was stealing from her parents, was staying away from home most of the time, and only dropping in from time to time. My sister took the girl's stuff and put it in the garage, and turned her bedroom into a sewing room.
Technically, my niece was homeless. But the reason wasn't Reagan/'the wealthy'/budget cuts/Republicans or anything else. It was her own fault for refusing to take even a minimum of responsibility for her own life.
A few years later, with a baby, a job, and an abusive ex-boyfriend, my niece moved into a friend's apartment. The plan was that they would share the rent, share childcare, share a car, and get themselves on their feet. That only lasted a couple of months. The friend moved out, while my niece was at work. My niece could no longer afford the rent, and she became homeless again. She moved back in with the abuser, just to have a roof over her baby's head.
Again, the reason for her homelessness was her own poor choices: Her CHOICE not to get any education past high school; her CHOICE to hook up with a loser boyfriend; her CHOICE to be a single parent; her CHOICE to work a low-paying job in daycare; her CHOICE to get into legal trouble over unpaid fines; her CHOICE to amass huge fines in the first place.
The former roommate had once also been homeless. This girl has a mother (with a house) who would have taken her in, but she preferred living in her car to being dependent on her mom. Her homelessness was certainly voluntary.
My niece now has an apartment, is paying off her debts, and is working very hard to pull her life together. She still can't afford a car, and has a stupid custody agreement that could mean that she would have to pay the loser ex-boyfriend child support, if the state of Wisconsin ever learned that he is unemployed!
There is a lot more homelessness today because there are a lot more people making stupid choices and expecting other people to provide them with whatever they need (food, shelter, $$) in order to continue making stupid choices.