Investing in  2-4 unit properties within the Dallas-Fort Worth metroplex would be ideal but I am also interested in other potential deals, that fall within the 2-4 unit range. 

I personally like to buy in towns/neighborhoods in which no new builds are possible within 10 miles because all the land is developed.

I saw once where a developer gave the buyer a pass on paying HOA fees till a house was built on a lot. 

I prefer to have the least amount of banks as possible.Create a bank account that you already have a relationship with(Credit card or mortgage)The least amount of bank accounts is also ideal.

My first self-developed software gave me efficiency.  

Think about what everyone else is doing.For reasons that I can’t quite grasp, someone decided that people who want to, need to, or have to sell their houses are the ideal audience to target.

The economy is stable—no wild bubbles or busts—and the city is attracting major investments.Elon Musk recently built the world’s largest supercomputer in South Memphis, Ford is investing $5 billion into a state-of-the-art truck plant to the east, and the Medical District is booming with healthcare innovation and development.

Given the scope of your work, a simple plumbing leak would not concern me, it's a $200 issue at the most and ideally, it's just another line item when you do rough in plumbing for the kitchen.Being in a Milwaukee suburb, I am guessing it's a 1960s ranch, probably with galvanized plumbing.

What Chicago neighborhood would be most ideal? 

I've had a long career in community development and have a lot of bank contacts that would likely be interested in investing, but I'd need to prove the concept first with an initial fund (there are also a lot of other community development tools that could be leveraged to maximize and scale this).