I voted yesterday that we will commission a retaining wall in the north during construction and initially leave the retaining wall in the south as is and then commission it later.
If it is absolutely out of the question for you to level the terrain differently than shown in the drawing in the initial post, then the proposed retaining walls will be non-negotiable both in terms of their nature and the timing of their installation, but urgently advisable. However, given the already not insignificant costs estimated for this, in my opinion, you should be more open to alternatives. Raising a house because one has classified a slope protection as retrofittable will be even more expensive.
the roof shape has no relevance for fitting into the surrounding buildings!
But the pitch, and indirectly the shape: with gable roofs of, for example, 35 degrees in the neighborhood, a 30 or 40 degree hip roof, clipped gable roof, or even shed roof is feasible, but a flat roof aka 2 degree shed roof is not.