There are business rules you can add that will keep you safer and there are strategies that target desirable renters and what they want.

I understand that unemployment is a major one and understanding what industry employees the workforce in your target area bur what are the metrics used during your "litmus test" of an area prior to going to work on getting it under contract?

You could target your marketing that way and try for $600, perhaps.

Aside from my own tech entrepreneurial adventures (I am a web developer), I wanted to give real estate a shot and see what it was all about.

Could not stop myself from giving it a deeper insight after reading your observation.I prodded the whole website, services and inspected web, talkedto people to know the actual story.

The US RE is a clear target for the money.

Did you do a web search to see if their deaths were public record?

I think in this case the OP did what he could with a property not in his target market.  

That same house in Indiana (any area in Indiana) would be 2k or less (they have a state mandated cap of something like 1.5%.If you don't have family or anything in Chicago in those areas, I would strongly suggest you reconsider targeting the south side.

From there, I created a plan, and my goal is to purchase rental properties in order to implement a buy & hold strategy in secondary and tertiary cities that are rapidly growing.From 9 - 5 I work as a Technical Recruiter and am actually transitioning into web development after taking courses for the past six months.