So far I have binged on the podcast, about 21 episodes in 4 days, the podcast is basically a download to the brain matrix style.

I know its treated me well all these years and has led me to some pretty incredible financial adventures that wholesaling simply could not do.But if I lived in some of the rust belt markets or other markets were there are literally more homes than people to put in them. .I equate that as nothing more than being a used car salesmen.. price points are the same. style is the same.. once your done your done.Where real estate gets good is 10 to 15 years into it ALL of your business should come from referrals.. this simply will not happen in wholesaling.. wholesaling your just as good as the last sucker you talked into selling their house to you undermarket  :)

Both off market but there are some sub markets in Chicago that look real nice no matter what your style of investment is. 

I have no furniture, no dishes, no linens... nothing but my own clothes and some tools. 

Stuart only has a few area's that have a decent cap rate like "golden gate" which is a lower income neighborhood.To the op's question, affordable housing will never go out of style.

Any book recommendations for business or sales that carries a similar style as Kiyosaki? 

Hey JasonI would look at the FNMA Home Style renovation loan instead of hard money unless you need to get in quick.

Each dwelling has variables to consider such as light exposure, reflection/absorption, finishes & materials in addition to the style that best compliments the architecture. 

I think the first half fits my style better. 

Where to invest is a more difficult choice and a lot depends on your goals, your investing style and your strengths.