I don't think re-classifying a widely disliked building as "challenging" is doing anybody any favors. When you build a sidewalk for the public, you don't make it "challenging" by, for example, only making it as wide as a balance beam.

A building must suit its purpose, and part of its purpose is to mesh with its surroundings. You shouldn't build a building that looks like Megatron exploded in the middle of a neighborhood of half-timbered buildings, no matter how challenging it may be to the people who look at it every day.

And let's not forget, a lot of traditionalist design took into account a world without HVAC and other hacks. If you want energy efficiency, looking to solutions that tackled the problem in a more fundamental way is a good thing, rather than papering over the problem with technology.

But you are correct about McMansions twisting the vernacular. The crime I always see is how the garage is, inevitably, front and center. It may be a Neo-Georgian whatever around the front door, but right there next to it is the hallowed automobile temple, like a phylactery to the Saints of petroleum refinery.