Dilemma; Prospective Tenant with a Bad History

[Ryan Tessier]

One of my investments is a 3 story house with an apartment on each floor. A vacancy opened up on the first floor and the tenant on the third floor is moving in there. She's my favorite tenant, clean, pays on time every time for the last year I've rented to her. She's taking the first floor unit immediately so I have no vacancy or rehab costs and her fiance's mother wants to rent the third floor so I wouldn't have any vacancy or rehab costs there aswell! Background check the mother in law and what do I find? Two evictions in the last three years and her income is 60% of the rent.

Now, every part of my conscious as an investor and landlord is telling me absolutely and categorically NO. But my sense of morality is pulling me in a different direction. Her son, daughter in law and the DIL's family are all vouching to support her financially so that the rent is no issue. She has an opportunity to live close to her son and put her life back in order. Looking at the mother in laws application there is no landlord in the state that would accept her in their right mind. She has no options whatsoever and she's still living in the house from the most recent eviction (state agency came in paid the back rent in exchange for withdrawing the eviction case, yay Connecticut) according to her the current landlord is a slumlord and a tyrant.

Currently where I'm at is the only way I can accept the MIL as a tenant is if the income earners from the family cosign their lease to guarantee payment AND agree to pay a year upfront in rent, with hope that her situation is better at the end of the lease term. This seems like a reasonable request but am I an idiot for even considering it? I've had some ugly evictions the last few years and really not in the mood to deal with another one. Have any landlord given someone a chance and had it work out in their favor?