I think if you ask some of the most experienced and successful real estate investors you will find the vast majority of them delegate most of the grunt work.  

I don't want to completely generalize but in my opinion, the vast majority of the time there is no chance. 

To save money I might try the library for a Quickbooks book.

I live frugally so I would save the vast majority of that money and keep doing bigger and better deals. 

The vast majority of the time the bank will pay the liens off when transferring to you.

Investments are being made to improve the area  but it's a long term bet.Jackson Park- Recent decision to put the Obama library on this site so it may be a good mid term bet.  

Chicago is a vast area, especially on the south side.

I currently own Frank Gallinelli book and I will look into adding the other two books mentioned into my growing library this week.Could explain the factor mentioned above "natural barriers to expansion"? 

@Chris Nordella There are many tricky areas in Indianapolis that vary VASTLY from street to street.

For me, the decision to move here was mostly because I wanted to live an extraordinary life where I can absorb lessons from a culture vastly different than my own.