The people that rent around here are high quality and the rent should cover expenses without any problems.

If you are set on flipping houses then you may want to find a quality flipper in your area and work for him so you can learn what the  process of flipping homes is like.

If that's what it takes to get quality numbers, that's what you do!

I have used Robert Reilly for both my primary residence as well as a rental, and he always did a quality job.

Looking for recommendations

You will counter more frame and stucco homes as you get into the outer areas of the Chicago MSA, while you will get a lot of high quality brick properties in the city and the surrounding suburbs (where I invest). 

Regarding final punchout projects, that may free up some of your time but it also gives you an opportunity to observe the almost finished product to help maintain quality control.

Often times, you can tell the quality of a market just by driving through it.

Does anyone have any recommendations for high-quality professionals in the following fields (preferably people who are themselves real-estate investors):1.

I would really like the help and will pay fair just looking for good quality work with good communication.