For us, the key is to invoice tenants for damages or service calls as they occur and to be on-top of late rent.  

We're also getting ice dam damage along the lower roof lines.

I have had tens of thousands of dollars of damage caused by 'good dogs' and "wonderful, loving" cats-some so severe that it was almost better off to demolish the property.Even if I accepted a substantial ( and by substantial, I mean $10k or more) pet deposit  I still run the risk of exceeding that if enough damage is done. 

Tenant accepts liability for alllandscape damage and/or replacement of such, if caused by neglect, abuse orlack of water.c.    

Does anyone have any knowledge about "Property Damage Inspector/ Occupancy Inspector" jobs?  

You may wind up with more problems from the evictions including property damage and law suits (tenant friendly Maryland).  

Since the roof is the Association's responsibility, is the water damage inside that it has caused their responsibility as well, or is it mine?

Loan limits can increase by a factor of 3-5 in many of these cases, but this comes with a major tradeoff of 3-5 percent "compensating balances" (read more collateral via covenants or less money loaned in effect)Item 2 is desirable from the perspective of reducing brain damage and consolidating relationships.  

I'm here hoping to learn ways of getting the repair covered because I don't think each unit will be able to fork over $3k out of the blue for the roof damage, plus I sense we now have damage to the electrical system due to water leaks. 

Again, ask your bidding contractors.3)The roofing decking should be thoroughly inspected from the inside (attic, etc) and outside (look for dips, bows, water damaged areas) for areas of the roof that may be wood rot.