Can you provide photos and drawings for better understanding?
Follow the quotes in post #2 and you will get to the other threads about the object.
Maybe the dormer and the extension could look similar, then it would already look better!
Yes, that would be the most elegant. A dormer starting from the "daughter" room, then carry the roof profile including the dormer 1:1 into the extension and also end the dormer there a good way before the verge.
We are seriously thinking about plastering the facade.
I repeat: SACRILEGE !!!
Painting over the bricks COULD also look totally bananas, right?
Only paint over individual bricks (virtually as "pixels") matching the (for example gray) bricks of the extension.
We are also aware that this will be particularly expensive!
You don’t have to make it expensive, but you can also follow my advice.
And get used to — also for the benefit of your own imagination — finally stop drawing the old outer (and future inner) wall so thin in the remodeling plans!