I know, it sounds ticky but it really isn't all that hard. 

As long as you don't lose all of your capital, throwing yourself in with the sharks could be the best, and quickest teacher.

Project management throughout the process. 99% of the time, buyers press a button to buy, press a button to sell and everything in between is done for them (including taking care of all problems, and selling it in the end) What was the outcome?

Almost all multifamily syndications will already be run as an LLC, in which investors like yourselves would be the passive "limited" members.

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.