While all of those are necessary to think about, none of these matter more than figuring out what goal you are trying to achieve.From your post, it appears that this is your former primary residence. 

I wanted to avoid all that since that (i am assuming) will make things complicated for me not to mention the timely payment of rent.i am in Chicago cook county and in loop..

Stop hanging out with your deadbeat buddies who spend all day drinking, talking sports, and otherwise wasting away.

All older, mostly 3/1’s ~1,000 - 1,200 sqft.  

You can buy the new property with hard money and perform the rehab, but all the funds used for the purchase and rehab need to come from the 1031 exchange and the loan, not your personal funds.

Purchased a condo and received an estoppel from HOA - had multiple special assessments identified plus seller's HOA unpaid dues listed and all were paid from proceeds at closing.  

Any and all advice is welcome and appreciated.

We added value by re-doing the whole house, installed vinyl floorings, rebuilt 2 and a half bathrooms, re-painted the whole house, replaced all the hardware in the house, installed new lighting, ceiling fans, re-painted the kitchen, and completely remodeled the upstairs.

There are teller notes on all my rent payment accounts alerting bank staff not to provide a balance on the slip if it is not the account owner making the deposit.I have used this system for 10 years with multiple buildings and dozens of tenants without any issues.

Hi all I am new to Bigger Pockets, although I have been a landlord since 2013 I am starting to treat this as a business instead of a side hustle.