I’ve been hitting dead ends as far as finding funding options being an out of town investor in the Pittsburgh area.

You could start there when it comes to finding out more about build quality and the types of materials used in the homes. 

(Approach - 2) - He says that if he is asked to pull permits, he is not responsible for any additional work that the inspector may throw (basically more money out of my pocket on the rehab costs).

Yes John, this is simply the purchase and rehab costs as my "cash invested".

Talk with your lender about this proposal...  1) Get a solid quote on the roof replacement and share it with your lender.    2) Put the funds in escrow with your bank for the sole purpose of replacing the roof.    3) Close on the property.    4) Install the roof.    5) Get reimbursed for roof expense out of escrow.Most banks are fine with something like this if they know their downside is covered.  

They're the intermediaries for a reason... they don't record the deed until the funds and all of the documents are properly filled out. 

A husband and wife were caught in a volatile situation—he ended up in jail, then came back out, and their home became a battleground of chaos.

Purchase price: $340,000 Cash invested: $7,000 Water front, 4 bed, 2 bath, detached 1 car garage, pier and dock.

Hey @Clay LehmanWe just did this today.1400-1800 sqft = 3 months of inventory$250K - $325K = 2.5 months of inventoryWe do 200 sqft differences and $25K differences for each analysis, I averaged them out to keep this reply short. 

I bought both of them cash money and should be receiving the deed in February because it takes a while to process.