Hi Everyone,Could someone please recommend me a good general contractor and an inspector in the Chicago area? 

The site inspector will just check to make sure you have a few basic things (i.e. a locked door for the premises where credit reports are accessed and stored, a locking filing cabinet to safeguard the reports, and a shredder to destroy reports no longer needed).I'd recommend anyone who plans on doing landlording long-term to do this. 

Just wondering is now the time to ask for a house inspector to walk through with me?

If it's not too bad then you may be able to get the roof 'certified' by a roofing inspector.

A good inspector will find those though and it's just something to be aware of, not a rampant problem at all.

We had to open walls for inspectors to approve work on a bathroom that was never permitted in our home. 

If so they have plenty of home inspectors and in many states (IN is) this is a licensed and regulated field.

With a HML each time they fund a repair they send an inspector out and then give you draws each time.

Maybe hire a Home Inspector with construction experience. 

Since I have done two live-in flips I also have a network for contractors and inspectors.