This is something that could easily cause bad blood in the relationship and for me, that is just not worth it. 

I will say that if I am the only one reading the ongoing saga, it still is cathartic to be able to vent the emotions on this forum.Keep in mind when working a deal that each deal has its own life blood, ebb and flow.  

These are blood-suckers going after the pot of gold because they know there's a very good chance they can scare the Landlord into an out-of-court settlement, wherein they'll get paid handsomely.

He was the only blood relation and thus the judge ordered all assets to go to him.

I've spoke with the city probate clerk about becoming administrator of his estate, but since I'm not a blood relative and not his next of kin it's been a bunch of jumping through hoops.It's been a challenge trying to do anything regarding his affairs, because of course no one will talk to me without the admin designation.

Nothing major (sheet rock was a little off, insulation he was using was thinner than it should've been, etc.)

Be really confident with your numbers and if helping this man can offset a slightly thinner bottom line it might be worth it.

There are items missing and damages to replace the front door, amongst other things like blood in the hardwood floors, etc. - should I file a claim?

And in 10 years when my Subaru has 250k miles on it and smells like blood, sweat and tears I am sure I will have gotten my money's worth.  

If your rents are already higher than market, and you don't have common area care included in your costs, either you're trying to squeeze every last drop of blood out of this or you are trying to make properties that don't really work, work.