Today is officially my last day with my W2 employer and I anticipate this being the last W2 job I will ever have.

What happens when something (inevitably) costs more than you anticipate?

my neighborhood in Chicago we're currently marketing for $1,350 and are getting more inquiries than we anticipated. 

Owing more than you anticipated does not make the title nonmarketable.

I hope that makes sense.You can look through similar recently-sold properties and calculate the prevailing Capitalization Rates in your area to get an idea for what to plug in as your anticipated Capitalization Rate for the purposes of the formula above.  

We anticipate having it fully rehabbed and marketable within 2 weeks or less.

So while a property in another state may so superior cash flow the appreciation is anticipated to be flat.

Fast forward to after closing and all of the sudden I needed all these things that were not anticipated.

Many large investment companies and financial advisers seem to anticipate lower returns at least right now; for the year 20XX, who knows. 

If it takes a week to set up the LLC, then start it a week in advance with the anticipation that you either are going to sell the LLC (and are ready for it), or your are keeping the LLC and closing on the deal yourself...which leaves the property in its own LLC, and separated from all your other assets.