The issue is and what Ootori doesn't get is that Midari's end goal most of the time she gambles is to commit suicide via gambling. That's how Yumeko was able to enthrall her because she saw through her ploy and "cucked" at the last moment in a display of abandonment play. Midari's just constantly playing 4d chess in an attempt to set things up which will enable her to die while gambling which is why she has reverse uno'd Ootori here. But I think what will ultimately end this series and the relationship between Midari and Ayame is that Ayame will care enough about her to save her and Midari would likely see that as a massive betrayal.