If the roof is damaged to where it is leaking, definitely do an insurance claim and fix it along with the other damage. 

I paid too much for my 2nd flip and shortly after I started on it found all of the termite damage and plumbing problems and on and on. 

On top of that, I will pay him $1,000 after he leaves pending an inspection to insure he does not damage the house. 

You're talking about $25-$45/sf depending on the amount of damage.

I have seen the damage done to sellers that trusted them only to find out their house wasn't really sold.Correct me if I am wrong--but didn't your profile state "wholesaler" yesterday?

However, a lot of the properties are extremely overpriced considering the damage to the homes.

Sufficient reasons to withhold rent would be broken stove, ceiling damage, etc… If the court rule the repairs are needed the landlord will be required to make the repairs and the tenant must put all of the rent into a court appointed escrow account.

With the plumbing being one of the major issues, you've probably got a ridiculous amount of rot and foundation damage and it needs to be torn down and the land needs to be regarded. 

EvictionI would leave eviction to last resort as this may cause more damage than good. 

The property is near Ohio State University and rented to students which leads me to believe that a lot of the repairs are going towards tenant damage, is it possible to write certain clauses into the leases that would have the tenants pay for any repairs they willingly caused (i.e. broken doors or windows)?