We purchased a two flat investment building in Chicago, Cook County. Both are section 8 rentals.

I’m having a lot of trouble with a tenant, withholding rent, and  giving 30 day notice (which would work out as 2 and a half months  rent she would be withholding the way she planned it out.)

I didn’t see this coming as she has lived there 7 years and we had a very close relationship. But looking back now, I guess I should have.

She has a history of being very late with rent, I’ve never charged her late fees, nor did we raise the rent on the unit the entire time she was there. My big heart got in the way. She is in her 70’s and we lost site on investment vs heart strings. In 2016, she went three months without paying rent, and again, heart strings. I did end up giving her a 5 day notice at the three month point, and she did pay.

My problems is: She is withholding rent because she claims we owe her money for an overpayment ($700.00) she claims she made...in 2012! It is not true, but she’s going with it. She clearly planned this out,k owing she was going to give her 30 notice, in addition to the fact that she will no longer be needing the section 8 voucher as she is moving in a nursing home. So she has nothing to lose in her mind.

I’ve gone through all the steps with her, telling her she cannot withhold rent based off something she “feels” is owed to her. And she would have to go through the proper steps if she feels this money is owed to her, it’s not legal! It has all gotten me no where.

I mean if her claims where true, why would she wait 7 years to bring it up. The story pretty much explains it self.

I do plan on giving her a 5 day notice tomorrow, and I have notified CHA. She also had her granddaughter move in May of last year, and she told me she reported it to CHA, come to find out she didn’t. They said she made a phone call  inquiring If her granddaughter could move in with her, as her caretaker, but she never followed up. So now CHA enforcerment is also involved. Found out her son was also living there for the better part of 2018 AND paying the rent.

But I don’t know what to do, or how to get her portion of the rent from her. We also believe she is moving to Florida, to be close to her sister (she’s mentioned this in the past few years)

If I give her a 5 day, it’s not going to make a difference,like I was explaining above, because of the fact she’s moving anyway.

And even after those 5 days are up with non payment, I could start the eviction process, but again, where’s that going to get me with her moving out anyway. I mentioned her possibility moving to Florida because I fear if we do take it to court to sue her, how would we track her down. And even if we did, how does that work if she’s out of state.

To make it more confusing for us is She sent me a text 2 days ago to tell me she broke The attic door. She said she would have her son fix it, I told her not to have him touch it (it’s an older home in Chicago,and it’s not a standard size attic door)

She sent me a text today asking me if I wanted her to pay for replacing the door. I have not replied yet because I remember another situation I was in,helping a friend. It’s a long story, but what always  stuck with me was when the detective said “if someone owes you money, and you take ANY form of payment for something unrelated, it would void out the bigger issue”

Like, I think, in this situation if we where to take money from her for replacing the door, we would be accepting the fact she’s not going to be paying rent. In addition these type of things are usually dealt with when we do final walk through with her.

She told me she has been talking to an attorney, I don’t know if it’s true. But if she is getting legal advice, it sure sounds to me like she may have been advised to do this, as a set up. I guess all of what she is doing.

I truly apologize that my question(s) are a lot,and long, I hope I  conveyed them in a way that is understandable.

I was just wondering if anyone else has been in this type of situation, and any advice how to handle it.

We’ve been lucky with our other rentals that we’ve never had to deal with something like this, so I’m at a total loss.

I will say though, it’s been a very good/tough lesson for us moving forward as to loosing site of the investment in the first place.

Thank you in advance for all that may have been in a similar situation and can offer any  advice.

Lisa