The property taxes on this building seem far to low for what properties typically pay in Cook County. 

Brian, I don't think investors WANT to see 50 or 100 houses before they make an offer but I would make a couple of points:1) As I tell my life partner "you have to kiss a lot of toads" before you find the right one but this is related to how you find the home...meaning if it is on the MLS - typically harder to find a deal although not impossible, if you drive for dollars you might have to look a lot of owners up but if you get to the point to see one odds start to flow in your favor2) If what you refer to is being a newbie and trying to understand what a good deal is or is not and if you have the time, touring that many properties to get an idea of value is fine.I have a w2 job and family so never had the time to specifically look at 100 properties with no intention to buy --  this is in no way a requirement.  

As is typical, companies operating at a loss have a high failure rate when we enter a recession.

This is typically used in divorces where one of the spouses moves out and buys a new home.

Is this typical for when a tenant vacates the property early?

One thing to look at is the water and sewer... that's a large expense that would be good to get in the tenant's names if at all possible, especially if that's more typical of the area anyway. 

If a typical 2bed/1bath unit goes for $700 in your market, it may be hard to rent yours at $750 to defray the costs of mowing.

Is this typical of AZ auctions?

Typically, you will be able to tell within 30 minutes if you have the comfort to work with this person for a length of time. 

I just wanted to hear thoughts on how much you would typically assign for before you go for a memorandum of Contract or double close.