The bigger question is how much do you have in reserves to cover yourself should you find yourself in a downturn - which leads to another critical question regarding cash flow.  

Great job, just be sure to screen those tenants well.... 

There were no recent comps, though the neighbors property 2 doors down sold for $290,000.00, in August 2013, so I knew we were on to something.We picked up the note for $9,850.00, and covered the past due taxes of $4,479.90 to keep it from being lost.

Good tenant screening will probably be very useful and necessary to ensure that you don't get stuck with problem tenants, even if it is only for a semester or two. 

If the roof is in working order they have no legal reason for not covering the roof.  

If the cracking is simply along grout lines and there are no raised edges, you could probably cover it with the vinyl (it will be hard underfoot).  

It will also cover most of the closing cost if the deal falls through and I need to dump the property, preferable to a wholesaler where I can avoid real estate costs.

When I asked him about his pricing, he stated he needs $178,000 to break even and cover his mortgage.

How will the other 5% get covered?

Other things to consider, especially in the Chicago market is parking...especially covered.