I know that they have a ton of upside, however I am unsure of the rules/regulations surrounding them and possible limitations surrounding how many one can take out.

We are very familiar with the city and surrounding area.

The biggest repair is a section of the flat roof that has water pooling and has deteriorated in comparison to the surrounding roof.

How should I start investing in real estate in Chicago and/or surrounding areas?

There are plenty of chain stores there now though, and the surrounding area of Portage Park is a good place to invest. 

They have largely failed because they think technology can solve everything and do not build the appropriate services and education infrastructure around the tech core of their model.  

My questions are as follows:What is the Market like in the area and surrounding areas?

Always up for deals in Dallas or surrounding areas, also I have about 2 other investment friends here in Houston area ,always looking

We did set the infrastructure for charging stations.  

And give them priority over non occupied InvestorsSecondly, the best way to overcome any fears and get comfortable is by running the numbers and surrounding yourself with a team of experienced professionals.