Unfortunately, it doesn't actually tell you that information: it just turns a dial. What you want is to know how much that dial would be turned by bad weather.

As long as it's not changing the form of the buildings, it seems valid. Although, the first two examples both add random telecom cabinets in places that don't make much sense.

Its not valid because it adds things like cracks, dead plants, patchwork repairs, rust, random utility boxes, loose cables, etc. Its won't tell whether a place will be maintained well. It gives you more of a worst case.

I figure that’s an architectural in-joke. The engineers will add ugly stuff because you didn’t consider stuff like HVAC or electricity.

Depends where you live I guess. For me that looks exactly like November here