Your the best judge.. within 5 days she'll either be gone or within 6 days you'll file on the upcoming Monday.. loss of processing for basically a week is what your asking..and court costs.. if you can avoid that and she acutally leaves.. your ahead a lot of timePersonally my gamble would be to meet her Sunday set the appointment up and get the keys. 

This jeopardizes the potential flip and is an awful gamble.

Next, consider your controllable and uncontrollable expenses monthly for the trailing 36 months.

I have been questioning the plan myself, as it seems like a gamble hoping the ARV is appraised to my liking (or my numbers' liking).

Unless you're dedicated to fundamental investment (and have the time to research/learn accordingly) you're (sort of) teaching gambling.

The condo itself was cheap compared to same-sized units in other places without board-ups, so I was willing to take a gamble if it wasn't for the potential insurance problem.

Seems like such a gamble to me but I really love the place.

Owner-occupied ratio no longer met, HOA being sued etc.So in essence it's a gamble anyway when hoping for a future sale process being smooth when talking about Condos.

BTW I spent about 7 years working in Black Hawk and never lost at gambling.

I think @Brad Larsen also gave you some great advice about the benefits of a career in Property Management as well as advice on taking a gamble on yourself, the way he did.