How soon is too soon? - MKE Eviction

[Tyler C.]

My tenant moved in July 2019 and has been 8-12 days late on rent every month, disregards my notices and avoids me like the plague till she's ready to pay. I'm househacking (living in the upper unit) and she goes out of her way to avoid me. We're conveniently never home at the same time when rent is past due. October rent still hasn't been paid, I've sent emails and messages about re-evaluating the lease agreement/setting up a payment plan and she still avoids me. I've always encouraged strong communication with her and she either won't respond or gives false promises on when she'll pay. I honestly don't think she can afford the rent now and I plan on filing for eviction next Friday when the notice expires (delayed due to weekend and holiday)...if she doesn't pay. If she does pay and next month is late (which it probably will be), I plan to give a 14-day notice and start the eviction process. 

I could put up with the late payments, but her lack of communication is really bothering me...especially when I'm trying to work with her. To make it worse, I looked on CCAP (to see if I missed something in the background check) and new eviction case from a property management company was just filed against my tenant on 10/3. Am I over-reacting by wanting to move forward with an eviction 4 months in to a year lease ?