A "middleman" would be the wo/man between an asset seller and an asset buyer, who generally does not change the basic asset but facilitates the transaction in some fashion that (theoretically) adds value.

I totally agree with Nick Rutkowski about starting off local to learn, as you will be able to resolve alot of issues hands on and in a timely fashion so they do not escalate into something greater.

The buyer has an FHA loan and I’m curious to know is there a difference in between FHA vs Conventional loans as far closing the deal in a timely fashion?

Basic 3x6 white subway tile with black trim is my favorite, old fashioned look for old buildings is right.

I am looking for recommendations for a CPA in the Chicagoland area (call me old fashion, I like to meet people face to face) that is familiar with Real Estate Investing for Rentals, especially after the 2017 tax changes.  

To be clear: The ultimate downside risk is that the tenant comes back and sues you for her $20,000 worth of jewelry and $10,000 worth of heirloom china that she claims she left behind.

or could you shadow someone who is successful, learn from them as you figure out where opportunity is and in what shape, form or fashion?

Creativity, problem solving, and ingenuity will lead to great wealth and success in real estate.2) Relationships: Real Estate is still a very old-fashioned industry in some way.

Manco,To add to Aaron's great response above, the reason your agent responded in this fashion is because they don't actually "underwrite" your account. 

I see you tagged Naperville, which is a great spot if you want to focus on single family homes in some fashion.