I am gonna give you my hard, but experienced opinion - because I have helped 2 homeless people in the past few years…
Does this person have the mental capacity to work at all - anywhere? That makes a big difference.
Plus he does have a criminal record, which does speak volumes in my book. Yes, we all have done some not too nice things in our past, but criminal???
I think there may be a correlation between some forms of mental illness or depression and homelessness. (My opinion only)
My ex-husband is a homeless, unemployed man. He is mentally ill. For many years after we were divorced I tried to help him with lodging, money, jobs, food and as much support as I could muster to get him on the road to good health and self-sufficiency.
It never worked. I would help him and he would inevitably do something outrageously odd - like lie or steal something. There is always the danger factor too.
My second attempt at helping a homeless person from my church this past year turned into a horrible situation of being really used and taken advantage of.
Recently, a 3rd homeless person approached me for lodging in my home. After listening for hours to her story, I fear there is some mental illness as well. She spoke of the police visiting her old home several times, child protective, etc.
I encourage you to take a loooooong hard look at this. You are helping the people who currently live under your roof. That is a blessing for them as well.