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.

Doing deals gets into your blood!

You can get a gift for a down payment but it must be from a  blood relative or "like" relative  and the you must explain the close relationship and why the "like" relative would give you a gift. a GIFT for downpayment is money given willingly to a buyer without repayment. 

Way too extensive for my blood.

Comming and going you are screwed to continue trying to get Blood from a Stone with Flipping, after Taxes. 

However it could be worth 170k-180 if everything was fixed and I think I could get it going as a functional rental property for the purchase price plus another 20k and some blood sweat and tears and maybe could get it reappraised in a year and do a heloc, but I could end up being 160k in when you factor in lost rent and is 10-20k inequity worth the gamble? 

You can't get blood from a rock, but it sounds like he would be able to cover your extra expenses assuming you won your case against him. 

For three or more unrelated by blood or marriage, I require each individual to make 2x the monthly rent.