Am I missing some fundamental here?

It is a competitive market, so deals are hard to find no matter how you define them, but stay at it and be disciplined about it ... strong supply & demand fundamentals cut both ways; that which is hard to buy in the short term is generally easy to sell or rent and tends to appreciate in the long term.

I agree with Taz about this fundamental mis-assumption: rent = 10% of purchase price.

I really need to get something fundamentally clear here.

Both office and retail real estate are fundamentally changing. 

Chicago fundamentally has some financial issues and incredibly high taxes. 

Your former teammates would be the first people to approach.I believe if you think big, do your homework, and master the fundamentals, you could have a huge future in this business.

I also happen to be at a pivoting point in my professional career and thought that a move into working in commercial real estate would be a great idea to learn some specifics of the business.My background is in logistics/process improvement as well as teaching and I wanted to know if there were some roles that could really help me lock in the fundamentals of the commercial space.

For that matter, join fundamentally any REIA in the area, but I know Bernadette's local to you but with a regional presence.   

It's really scary about how big real estate really is but I know that with solid fundamentals, I'll do just fine.