Landlord here: I've a new tenant moving in next week and during the walk-through he points out some minor issues on the walls in two of the rooms (previous tenant hung pictures so there's some pin holes and marks on the paint).

I have some holes in my knowledge and paying a giant chunk of money to HOPE someone can help me.  

All you have to do is plug the holes".

Mechanicals, foundation issues, sink holes on the property, structural issues, etc. 

Its like sticking a square peg in a round hole.

When an applicant pulls up in a car full of bullet holes...automatic denial?

Depending on how your P&S is written, the seller may be able to sue you for specific performance (compel you to fulfill your contractual obligations) and possibly monetary damages if your unreasonable delay or breach of contract has caused some other loss to the seller, like losing another home that was to be purchased with the proceeds of this one.Frankly, I would try to get the deal done and avoid the headache of lawsuits. 

Once you have done the paperwork the Federal or IRS lien group will ask you for a monetary amount or work something out with you. 

Ohio law has more protected classes than anyone and it's not just monetary damages, he might face.Especially if he's a licensed real estate professional or has more than 4 rentals. 

Busted windows, patch work (holes punched in walls), replace garage door....