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. 

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

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..

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

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

Any and all advice is welcome and appreciated.

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.  

If they are filing false complaints it’s one thing but if it complaining and it’s true, even if it’s minor in nature - that’s more an Airbnb issue and they know how to game the system.Reality to is if you get them to stop whose to stop them to ask a friend etc.Your best bet is to talk to them and find out what the Cruz of the issue is

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.