@Stax I'm not sure if experience professionals can resolve it by looking at photos, but at least they can give some valuable advice or if there's any obvious flaw in the proposal. I'm talking to some roofing companies as well, but think the input from an online community is still quite valuable.

I'm in Richmond, VA, and it rains heavily when hurricane comes.

Gotta love the disappearing replies........................

The issue is a design and structural one, not gutteral. That is a huge amount of water damage that has probably already happened. And will continue to happen. Until the whole area is redesigned. Gutters won't do it. Way too much water channeled there against the house.

The architect was too creative...