I've read most of them and they'll give you a comprehensive overview of how the RE industry works and how you can use it to quit your job.https://www.biggerpockets.com/store2.

It is not clear how they are making money and-my best assessment is they are losing each month?  

Even though it's a condo, you'll still have inside things to do as well as the risk of a dreaded special assessment.2) You're planning to self manage?

The basic formula is (total municipality expenditures) divided by (total assessed value of all property in the city) = tax rate applied to all property. 

I haven't done anything like this on a home and I know it's different from a car, but on a comprehensive car claim I've had the insurance offers me a number in cash and I asked for the repair to be done with their licensed shop.

Find out when the last assessment was/ how much was / when is the next / how much money does the HOA currently hold. 

Since I’m a newbie I’m not sure what i should be looking at or what questions to ask so that i can properly assess whether this is a good investment or not.

thoughts on how to assess safety?

I don't think this needs to be complex though, you could just as easily keep a notebook where you have a page for each month and keep a list of who paid how much on what date, late fees assessed/collected, etc.

I agree with the sentiment above, CAP is important, but the main thing to consider in Illinois/Chicago is what is the current assessed value?