Trying to avoid the occupant from potentially damaging or trashing the place just to get even .   

No credit to damage...or to save.

The security deposit is for damages , tell them no and start the eviction process

I'd rather have 3 busted potable water lines to one damaged yard sewer line any day of the week. 

To name a few HVAC for unit 1 is 20 years old and could not fully inspect the heat, the pipe to the sewer has completely dropped and is not connected, in basement the window header, subflooring and joists are damaged from termite activity, and their needs to be some tuckpointing and masonry work done for the exterior brick. 

I wasn’t picking on the way you said it.Would it shock you that there are attorneys out there now who specialize in going after private lenders, claiming their intended business-purpose loans are really for a consumer purpose and subject to all legal penalties, damages, and consequences?

It can also capture damage to the property for which the tenant will be responsible so they don't claim it was in that condition when they moved in.

Not having the correct team and systems in place and totally damage your reputation as a property owner/manager, if your team (the maintenance company) does not have the same vision as you.Perhaps there is someone out there and if so . . .

Also how do I make sure all secondary damage such as gutters, siding, windows etc are covered and accounted in insurance claim.

On another occasion I had them inspect the property after purchase and they informed me that due to the condition of the roof they were raising my deductible on any roof damage to $5K instead of the $2.5K for the rest of the property until I installed a new roof.