Assumed nothing could possibly go wrong in the next 5 years what you want when you look at an investment property is to know the current rental amounts, specific expense items, and conditions of the building, grounds, and mechanical systems.  

I like your post and you obviously know Chicago but a lot of what you are saying is just plain wrong.

Should Temp dip below 32 the pipes would freeze and then burst costing thousands of dollars of damage.What exactly is it you think the property manager did wrong?

I corrected it and then clicked post and found when it prompted me to create a longer headline it also 'reset' my category so it posted to the wrong category and it won't let me edit it :(

Everyone will give you wrong information wasting their time and yours.  

Depending upon your background, there is no right or wrong answer?

What can go wrong?

Being tied to the mortgage or deed post-divorce is a bad idea, we have personally gotten dozen of calls where things went wrong post-divorce when someone was still on the mortgage.

Am I looking at that wrong?

If they are wrong, well, you can buy that deal from them (or their lender after they foreclose) a year or two or three from now for less than they paid...By the way, there is nothing wrong with buying a single family home or duplex--my first deal was a mobile home.