Went through the LLC battle in my head several hundred times, and ultimately landed on an umbrella insurance policy as the band aid to hold over my liability anxiety.  

If you have never done a fix and flip before, convincing someone to be your partner may be an uphill battle because you might not have the appropriate resume material.

The third one has been an ongoing battle trying to get all of the stuff the previous owner fixed, actually fixed the right way.

I have been battling this concept myself.

However, if you are dealing with a normal seller without any experience, you're going to be looking at an uphill battle because investing may not be something that has crossed their mind.

Not letting fear win the battle and taking steps as I go along.

(He lives in same building as landlord)My concern is I'm reading a lot of scams on how Chicago tenants try to work the system and the landlord is stuck in a battle for months.

It's an uphill battle, in such a popular location. 

Other than that, it's going to be a constant battle between you and the tenants on usage.

I hear several time that I do not need to be an expert of the transaction and paperwork procedures, but I do need to understand what is happening and when it is happening ( we never go blindfolded for battle, right?!).