Late January, we get it rented out again.Between the process of eviction and the slowdown due to the holidays, it seems entirely possible that we'd miss out on 3-4 months rent by going with scenario 2, not to mention the expense and hassle of the eviction itself. 

We're in the process of suing the tenant for the back rent and damage to the unit and I'm guessing she called the city to report the violations to claim unsafe living conditions or something.

I wrote down my steps to begin so that I can visualize the process.

Then, compare them to your property.I'm in the process of buying another 3-family w/ a partner.

So as I'm processing everyone's responses, here are my challenges (in my head):1.

Rehab is done and in the process of doing a refinance for funds for the next one.

As a brand new investor, perform this process at least 5-6 times before you have a job in hand that you're desperate to start.

I am looking to start a group with newer agents in the area so we can pool our knowledge and shorten the learning curve so we all can close a lot of sales so we do not become statistics haha, hit me up privately if you are interested in networking and learning together.

So there are 1) very few scenarios where a deal makes sense, and 2) hundreds of other investors scrambling for the same deal when it does exist.With regards to short sales...A short sale is a long and drawn out (and often frustrating) process, and is not for the faint of heart, or for wholesaling, in my experience. 

If they do not pay for next months rent, start the eviction process right away.