I currently live in it as my primary residence but had plans to eventually rent it out and then cash out refi once I reach 20% equity in the property.

You will also provide the whole amount if you plan on repaying the loan in full beforehand.  

The first thing I ask is why am I Buying the property.I always look at the exit strategy first, is it going to be a rental, a lease option sell, am I planning on living in it.

I plan to make them into rentals by this fall.I’m looking to connect with someone who want to work together.

We just gave our tenants notice that we are planning to move into the rental they are leasing from us.  

There are some teeth to HICPA since it works in tandem with the Unfair Trade Practices and Consumer Protection Law ("UTPCPL").

I had a similar strategy with my first few house hacks: buy in great A & B Chicago neighborhoods....get by with minimum cash flow, and wait...What's your plan for the next purchase Michael?

I am on commission only compensation, so I moved back in with my parents, and am trading all of my time (60-70 hour work weeks) for little/no money. 

You understand some of the basic concepts, but also have some giant holes in your plan.

Depending on your credit score in the US and credit trade line history, you could put as low as 25% down.