The reroof is causing a vapor barrier problem as now you have 2 vapor barriers in the same plane and traps moisture between the 2 layers.   

That causes me to be concerned about the type of insurance you have on the property if you ever have occasion to file a claim.

This caused some complications, since if you don't have students lined up for the unit on Aug 1, you're probably out for the semester.Here is everything that's gone wrong or been a substantial disappointment:1.)

I care a lot about my clients and I also donate 10% of my earning to environmental and social causes. www.dogoodre.com

Would this ever cause you distress"?

Yes, but keep in mind that a leaking roof would not be covered unless there was an "Occurrence" that caused damage to the roof. 

We are sorry for any difficulty this has caused you.

Have any of them had late payments in the last year, or caused any problems you dont want to deal with? 

If it's just cosmetic, I'd mask it and bandaid it rather than potentially cause mechanical problems. 

This is important to avoid getting in trouble with a contract that was poorly written causing your deal to go south.