Early failure is when hings don't go as planned at the start of something new, like a project or a job.

I like that plan, I just don't know how many properties my wife will let me have with negative cashflow each month! 

If so, you could plan to market about 60 days before lease end or even sooner if their house is ready earlier, so you can close as soon as they are out.

I pitched it to my fellow investors, but numbers did not work for them and we did not want to purchase the house ourselves, our initial plan was an assignment.As time passed we decided this house needed to be listed on the MLS to get a retail buyer.  

Hey @Jacob Munson, so you listed the basics just to get the house.You have plan to outfit the place like @Alex F. said.

The plan is to put it up for rent for ~3000$ which is lower than other places in the area.

I think to better answer this question for your specific situation, I would like to know where you'd plan to live and the cost you'd acquire monthly for your new living expenses.

All of Chicago is not falling to pieces with crime.I'm happy to connect, understand your goals, and see if we can add value to your plans.

Are you planning to visit the sight often?

@Marcus Robert Depends on what your plans are.