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Inexperienced landord, in over my head

Posted Aug 2 2022, 08:36

This is my first time being a landlord and it's safe to say I'm not very good at it (yet). I came across Bigger Pockets a few months ago and am now seriously considering pursuing REI, but realize I need to change how I handle being a landlord. I'm happy to explain in more detail if needed, but the gist is that I rented a fixer upper that I bought (planning to flip) to a former high school friend who has trouble paying her rent almost every month. I've been renting to her since 2019. She has a 5 year lease with the option to buy. I clearly had no idea what I was doing, and thought it'd be an easy way to make some money while helping out a "friend" who was down on her luck. I didn't know anything about tenant screening and never considered that she'd be a nightmare to deal with. (I'm learning!)

She has rarely paid the rent on time and always has a long sob story that I seemingly fall for. But since the pandemic began she's not only been late on paying, but made partial payments and skipped entire months. Dealing with her has been incredibly stressful, so I was happy just to get anything, which I realize now was a bad mindset. Because of the eviction moratorium in NY I felt like there was nothing I could do, so I gave up asking her where the rent was and just hoped I'd get a check eventually. She applied for ERAP last fall and I received $5,500 in back rent in April. Unfortunately, this means that she cannot be evicted now for another year (maybe I'm lucky she's been paying rent at all). 

I just received July's rent check today but still haven't gotten June's. She says she mailed it out in June and had a long excuse for why she doesn't have the money order receipt anymore so she can't track it/cancel it. Basically she said that she sent the check and there was nothing more she can/would do about paying for June. I told her I'd like her to switch to online payments with Avail so that checks can't get lost in the mail anymore. Her response was that she doesn't trust the website because she's never heard of it, she doesn't have a checking account anyway, and won't pay the 3.5% fee to pay by credit card. 

I know I've handled her entire tenancy badly. So now I would love some advice on how to fix this mess I’m in. I feel like I've set a bad precedent and I'm not sure how to correct it, if I even can. I learned from some Bigger Pockets books about the importance of mailing late rent notices, which I'd never done before. Except that now that she can't be evicted for nonpayment for another 8 months, it's not like I can threaten to evict her if she keeps mailing the check late. Do I start sending them out anyway, just so there's a paper trail? Do I just wait it out and evict her once the moratorium is over next year (as I'm sure she'll continue paying late), and hope she keeps paying in the meantime? How do I handle late/nonpayments at a time when someone can't be evicted? Particularly the "lost" check for June? Is there some other more reliable way to get her to pay if she doesn't have a checking account? I do feel bad for her situation and don't want to have to evict her, but I don't know how to train her to be a better tenant, or if she's untrainable...I’m really at a loss for how to deal with her. Any advice would be greatly appreciated!

Upstate New York, New York

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