Which equates to an potential expense even for small simple matters (applies in city of chicago). 

Anyway, a simple question in for rent ads saves us from all this drama- how many animals?

I found out that if i pick openlisting.com or reali (reali just has a flat fee), i get maximum returns from buyer agent commission. 

Not familiar with your term, "house hacking" but I'd recommend picking a few ways to learn and profit from real estate.

The course should run you around $300 but can be picked up for a discount if you search google for coupon codes.As far as free educational sources- youtube and podcasts!

There are a lot of good agents, PM inspectors and others. what works for me not necessarily will work for you.each one of us come with different agenda and plans.I recommend you to pick up the phone or email and reach out to some of them. share your plans and ideas for the near future and the long term. remember, its all about the people and the connection you make, once you find the right one for you, eventually, your team will build your team.good luck.

Is it as simple as scanning the newest Chicago City Lease and appropriate disclosures and sending them the link through DocuSign?  

For you next investment I'd pick whatever investment aligns with your real estate investing strategy and goals for the long-term.  

It is because I picked a smooth talking contractor who I overpaid upfront.

It has three or four small units, not sure.Anyway, what is a simple evaluation for that property?