At 7:15 am, we do stretching and tai chi for 30 minutes and then he drives me back.

It sounds like you're stretching your finances too thin. 

I know businesses can be 3x revenue, obviously PM is more client facing so it's unique. 

You can stretch your budget further in the Bellwood/Berkeley area and a few of the South Suburbs.

Generally you can find deals in B/C class areas no problem with rents at 1%.I live here myself, 5 minutes from downtown and within the city limits, and would not consider it super dangerous by any stretch.

The reason the content I am studying won’t point me in the right direction where to start, is because I am in what is apparently a unique situation.

(If you're outside Milwaukee, feel free to chime in too - just wondering if there are unique needs in our area, but general feedback welcome too.)Thanks in advance for any insight!

He's able to charge a good bit of money per unit since it's a unique experience, and they should be relatively cheap to build once you have the land. 

A knowledgeable VA lender can provide guidance tailored to your unique circumstances.

#3 is the individual credible i.e. have they done what I want to do or have a unique perspective that will help me get to #1 faster?