I have a 2 story home where the first floor and rear area of 2nd floor are stucco. The front and half of each side overhang and are sided with T111. My roof is flat with a slight V shape and no gutters. This sends rainwater over the sides in the middle of the roof at the lowside and over time water got behind the T111 on both sides of the home causing paint peeling and some rot which is getting worse. Plus I'm oceanfront in "sunny" California so dampness in general is a concern. I must get the roof redone with hot tar and stone and I was thinking to just replace the T111 with stucco like the rest of the house. It will be tough because the home sits on a sloping abutment with a difficult scaffolding ahead. I assume the roof should be done first. Since the T111 is so bad, how do they attach the stucco? Should I replace the T111 until I get the Stucco done or would they just replace it anyway with regular ply or something so it would be a waste?

I had some damage done on two pieces of my vinyl siding. the question is how do you remove a piece which is between two windows and installing another piece. I have extra sheets to do this. Thank You tommy1