I initially planned for a lawyer to draw rental agreement which would prevent establishing residency.. apparently this is not possible in IL. 

Listing site estimates roughly $1,700 in mortgage, tax, & insurance with 20% down.What are your initial thoughts?

There is a difference between an infestation and there being a few stragglers of an initial treatment of the roaches.

My rental property was initially bought free and clear, but in July of this year I refinanced to pay off my primary residence because of the appreciation value that my home had basically equaled what I invested in my first property.

The initial purchase was with a personal loan of $40k from my bank (USAA) and the rehab was budgeted at $11k and financed by my fiance using her personal savings.

And yes, I’ve since bought a new primary so if I refinance my only option would be to refinance into an investment property taking the interest rate from a 3.75% to a 4.3% and the cash out would only yield 15k since I initially only put 5% on the primary!

Financials: Mostly COC return (NOI/initial investment)2.

The up and coming business in the area is just the cherry on top, lot of money and initiatives being dumped in. 

@Ken Dunn made some good suggestions for how to protect yourself in your initial contract next time, but in your case it sounds like you've already settled and the old owner doesn't have any obligation to you at this point.

I've worked to follow the Info Template above:I had a good year in 2017 and when time to pay the rest of the taxes in 2018 and after getting a call from a motivated seller, I instead made an installment agreement with the IRS and bought that initial Colorado 4-plex on owner-carry for $800K using that $50K earmarked for the IRS - for the down payment.