A contract with financing should work just as well to get more time.

It looks to me the cost of management was a key as well.

Do you know the area very well or have family/friends that live in the area?

On one hand, there're a number of legitimate tax deductions, credits, and loopholes that are not well-known.

For those that have yet to do this, it takes less than 10 minutes if you are a single member llc - just make sure to have a copy of some sort of identification. we did all of ours .. and our attorney contacted us as well and let us know to get them done or he would do them for us. 

I can imagine it is considerably more work as well as I plan to manage myself.

That never ends well.

I've heard having too much equity in one property is risky as well.     

I am happy to make some connections with some other Chicago investors as well!

You could put in a range of numbers for purchase price and closing costs, renovation expenses, and expected returns and you could very quickly get a range of projected return on investments (although an excel spreadsheet could easily do this as well), but I'm sure as technology develops we will see even more sophistication in AI's ability to assist in deal analyzing.