I'm trying to add on our old farm house which in terms of walls, is easy as we are just squaring off the back of the house. The roof line is complex as the house has been added onto several times. I uploaded a picture of the house now verses the only roof design I can think of that would work for that space except the dead zone being created by my circled area. I prefer not to tear off any of the existing roof if I can avoid that to keep cost down.
I was thinking of maybe adding in a fill area here but I don't know if that's feasible in terms of roofing, and all my roofer could tell me is you cant have 2 hips ending in a valley.
My only other idea is something like this: