Having professionals (real estate agents, inspectors, investors) around helps shield you from buying a lemon. 

The inspector likely asked the contractor something along the lines of "mind if I take a look around" or "mind if I come in". 

Let the inspector do their thing and negotiate those repairs later. 

A home/commercial property inspector may or may not be enough for the job, but you will need to get one regardless, so make sure you get a good one!

Granted, I'm probably fussier than the average turnkey investor since I am a contractor and home inspector and have rehabbed several homes myself.   

UNLESS you're a professional inspector, hire one to look for mechanical issues BEFORE you close.4.

Anyone that mentioned working in Chicago have an inspector they loved / caught stuff maybe a normal inspection might've missed but took up some of their built in reno budget?

The bank almost didn't lend because the house wasn't "livable" (with the 8x8' ceiling damage), and had to sweet-talk the town inspector to give a CO, due to the ceiling damage and a few cracked windows.  

When I pulled up I was met by the Board of Health Inspector, Living assistance officials, and two Worcester Police men touting guns and handcuffs. 

The inspector overlooked that part.