The idea is to invest in a smaller midwest market where the cash barrier to entry is lower, establish nice cash flow to then re-deploy into the Miami market where appreciation is the main driver for investment.

You have to give them time to cure.  

Curious if that is an established link.

TRIG is the bigger one on the southside, older, more established, not sure if there's a fee attached or not.

I was thinking of establishing the LLC, opening a business bank account and depositing $20k and using those funds to get a loan to purchase a home then rent it out, show that as revenue to a bank, and proceed to buy another home, and slowly rinse repeat with cash flow or breaking even with the long term goal being that the mortgages get paid off in 15 years to where eventually the renters go from paying down the mortgages to paying for my early retirement.  

First off you need to determine whether you're having basements which I'm assuming you are then has it been established and prepped for basements and  if they are formed. 

@Mark GallagherMaybe it's because I'm not established yet, but the rehab estimates I've gotten from contractors are significantly higher than the ones you listed.

Begin researching HELOC and work towards establishing credit etc.

The PM has established network of vendors for better pricing. 

If it were me I would wait until I could find something in a more established neighborhood more conducive to obtaining qualified applicants.