Personally here is what I would do in this situation--for what it's worth: I would bring in a contractor and get a price to redo this area of framing and put on a new roof (decking and shingles).

I am purchasing a home in Rexburg, Idaho that has a second floor deck/home addition that has settled.

I want to replace the deck/stairs on the back of my two family.

I'm sick of trying to figure out ways to mitigate my business risk when the deck keeps getting stacked in a unilateral way.  

Does it have decking or is it a cedar shake roof.  

I have waterproofed exterior stairs, decks and roofs/balconies over living space where it has to be perfect.

paint touchup around home, cosmetic stuff with brick flower bed, taking down a roap swing, removal of a deck in back that is basically a warehouse pallet, possibly some lawn care, etc.

Remove all flooring boards and replace with plastic decking for a maintenance free repair? 

I'm currently renovating a triple decker in Dorchester and am looking for a good contractor to repair the vinyl siding where we removed and added 6 windows total, as well as where old deck ledger boards once were.

The surrounding deck area and coping?