Six months ago, I started my RE journey with buying a 3-unit house hack in Chicago. When I bought the place, two units were already rented, and I'm living in the third. One of the tenants has been a recurring problem tenant, causing significant damage to the apartment, causing me to receive complaints from the other tenant, and consistently paying rent weeks late. As such, in March I kindly told them I would not be renewing their lease (which ends 5/31), due to needing to make renovations to their apartment (rather than telling them they were the problem). At that point, they begged me to stay, and when I refused they stopped paying. In April, I gave them a five day notice for nonpayment of rent, and filed for eviction with the county. From talking with him, he shows no signs of planning on leaving at the end of the lease. I'm in a very tenant-friendly jurisdiction, and as such the sheriff still hasn't served the tenants despite it being almost four weeks. I performed an arrest records search on the tenant and found a history of arrests, as well as a warrant out for their arrest (failure to show in court). With my own safety in mind (since I live in the same building as this guy), should I threaten to report him unless he leaves? At this point, I'm not looking to recover the $2000+ in lost rent, I just want him gone. I haven't tried cash for keys yet. Thanks in advance!
