My shop is a converted tobacco barn.
The window area was what was called a "stripping room" - they stripped the tobacco leaves from the stalk after it was cured by hanging in the barn. That was my shop for over 15 years.
The wood was getting hard to maintain and the roofs need to be replaced. Wrapped and re-roofed. We left all the original wood beneath the wrap so the barns can be returned to their old glory. I am not into wood maintenance!
The next year I converted the next two stalls into more shop room. Windows, A/C and heat. I hung panel door that slide since I wanted the head room for a lift I never put in. The door were a mistake. The stripping room door is to the left of the Mercedes and it is a pain. The doors will be replaced some day,
The next year I finished out the rest of the barn and used overhead doors on the last open stall and at the end of the barn. I really recommend the overhead doors for you place.
That is the area I am going to add windows to.
One last shot from behind.