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?

I invest in Indianapolis and, while I think it is terrific that this tool exists, I am not sure I agree with the assessments...at least not in some areas that I own property.

I am not saying it's not a worthy investment, I just think that if you dont have serious knowledge of the area and typical rental practices it isnt a fair assessment to just put some numbers into an online calculator and expect that you're going to be getting the cashflow you anticipated. 

In California there's Prop 13 that means some parents who bought their homes a long time ago have a very low assessed value for property tax purposes. 

If other condos in the area charge the same and provide more maintenance and insurance, they are probably operating at a deficit, not funding their reserves, and a special assessment will be needed when the roofs need to be done or for other maintenance.

I don't think his visit was a comprehensive site inspection (the lender separately ordered other companies to do a phase I, a property condition assessment, and an appraisal)--more likely it was part of their standard due diligence process for the lender's representative to lay eyes on the property before they lend on it.

If you wanted to assess with greater accuracy, you should deduct the carrying cost of the $33k over the time period it takes to build the new unit (ie, the money isn’t generating income, but costing you ~4% interest).