@Naftali Green the most tried and true method to make sure you don't work with scammers is by getting recommendations from other real estate investors. 

"The quality of your life is determined by the quality of the questions you ask yourself." - Tony RobbinsNobody cares what you are doing and just because people say you are "wrong" doesn't mean anything.

These cities tends to command quality tenants and they have great schools.

I like the KISS method and the idea of limiting the options. 

My investor is looking for a solid, dependable and quality PM, to manage a couple of units on the north side (Rogers Park).

https://www.biggerpockets.com/...
its discussed here that exponential jumps is key to building the cash flow and financial freedom, if you have, say 300k liquid, how many jumps should one make to jump levels, I have ...

Fully rehabbing the upstairs kitchen, bathroom, and living rooms with medium-to-high-end furnishings (to fit the area and future tenants), and basement will have smaller quality-of-life improvements.

Your most cost effective and fastest method is going to be to apply some pressure.Good luck!

It's better to have a property vacant or charge less than market to attract a high quality tenant then to get someone in fast. 

Are their listings detailed with good quality photos?