My initial thought was to start updating all new leases upon renewal, while this may be what I end up doing, all of my renewal dates are scattered far apart so I was hoping to get some advice on if there were any faster options to avoid waiting too long and causing reputation damage or lawyer issues in the long run where while I failed to do enough research I did not personally set these leases the way they are. 

We initially were purchasing a condo in Hypoluxo FL (close to family who are RE agents, contractors, etc) but seem to be falling out of escrow due to appraisal issues.We have some familiarity with markets in central WI (I'm from WI and the company I work for is there), Asheville NC (family), Nashville TN and the West Palm Beach area of FL (fam live there).

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.