I used to do custom remodeling after I got off the road as an entertainer
One time we had a big problem with parking at a project at the beach. Coastal zoning is rediculous whe you try to make any changes and they make you bring everything up to the new earthquake and other new code standards when you do any major work.
We were near the end of our project, there was still a huge nagging problem. there wasn't enough parking for the number of bedrooms. The square footage of the two buildings didn't change but we had to connect them some way or spend another 100 thousand to rework the 3 story garage building.
The problem was the two buildings didn't line up for a roof to connect normally and we could not impinge on the right stairwell opening (in the first picture's) height because it was the floor of the second floor.
you can see how I jogged the foundation to make up the difference in the offset but the tricky part was getting some kind of roof to work and not cut in to the head area of the rear stairwell.
The architect had a lousy solution which would have looked odd. I was sitting there studying the problem while the drywallers were doing the rear building and the roofers were tearing off the roof of the front house.
It came to me that we could skew the ridge and have the rafters shorter on that opening side so they came down at a steeper angle and dudn't cut into the opening.
The owners liked my idea and that's what we went with.
I suggest that you can figure out the problems of your quit in the same way you solve any other problem and not be overcome by it.
Think about what you're doing, make your plan and carry on.