Once I had the structure and walls sorted out, I decided I really didn’t want to get out on the roof and I was already 8 months in on this project. So I cheated.
I hired professionals to cut out the roof and build the shed dormer. Basically they finished the framing for me. They also completely dried in the structure, did the vapor barrier, shingles, and siding. While they were doing all that I found a “slider” window that met egress requirements and i had it delivered for them to install.
These guys knocked out in 4 days what would have taken me another 6 months to execute poorly and possibly with a lot of broken bones.