-Do I first set up a holding company to own all future LLC’s for each property?

Unless you are a veteran or using a DPA program all loan products require some skin in the game (down payment) and that is how most people start their portfolios. 

It is increasingly common for a PM to charge a "leasing fee" which covers all the costs of marketing, showing, screening, placing tenant under contract, collecting deposit and rent, setting up utilities, getting the tenant placed, etc.If the PM can't justify the cost, then they shouldn't be charging it.

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

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. 

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?

All I've ever heard is that GCE is an unconstitutional taking of private property.

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.

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.