How to best protect myself renting to a non qualified tenant with qualified roommate

[Lily Yu]

I am considering renting to someone who

1. Was a drug addict but allegedly clean for 5 years. Had a felony arrest 5 years ago. 

2. Has bad credit

3. Has no job

hear me out. 

his mother contacted me. He is living in their family investment home but she's selling it and she's looking for somewhere for him to go. She has significant enough assets. She is willing to sign on as the main tenant which means she is responsible for the apartment. 

my thoughts thinking out loud:

the other prospective tenants have income issues so at least in this case I know the rent will be paid. 

the mother has pretty significant assets (low 6 figures + another 6 figures from sale of the house) 

if he destroys the property I could go after her for it right? She would be listed as a tenant even though she would not live there. 

he has supposedly been clean for years. The mother would not be willing to sign on and risk her assets if she thought there was a chance he could relapse and destroy the place, I'd assume. 

other thoughts: say he has unsavory friends and starts inviting them over. So the rent is paid, but he is disturbing the neighbors, or stealing things, or smoking cigarettes indoors or something. He would be in violation of the lease and would need to be evicted. I'd have to hire a lawyer. Could I go after his mother for these costs? 

i want to give him a chance. I'm familiar with recovery and addiction and I know some people just need to turn their life around. But also need to protect myself.