What other aspects should I keep in mind and look out for in a property of this age and condition?

It's great to hear that you're interested in starting your journey in real estate at such a young age.

@James McGovernA D Class property is based on age, and location.

Congrats for getting started at age 21 and I really wish you a lot of success, but I have bought my first rental property in Milwaukee 15 years ago and frankly, the market was much easier back then, I did not have the expense of a PM and cash flow was solid at about $200, but not amazing.

We say when you are in the REIT, "you are in it to win it" but their hold is much much shorter than yours would be at age 41.  

In my state you have to be 19+ years of age or older to enter into a legally binding contract.

You don't know any roofers, so you just pick one out of the yellow pages (yeah, I'm showing my age) and they got 1/2 way done and then went to do another job and it rained, destroying your roof? 

To me there is a distinct difference between the two. 

The goal is to have control of my time and make memories with my family - especially while my kids still like me (ages 8 and 10).

@Andreas Mirza There are two distinct NPN markets in Chicago, residential and commercial.