"I have never in my 25-year professional career been asked to create such a roof, ever. I have used Chief Architect Premier through that time."
I guess that somewhat answers why Chief Architect has never had this facility and also why the building's architect did what he did with the roof - it appears he was looking for something new or different to convention. However, it seems it was not novelty simply for the sake of it. The ridge end of the roof is facing north while the base is facing south. At this elevation (10,000ft) the sun can be intense with substantial solar gain. Tall windows are therefore not especially desirable in this circumstance and large areas of wall without windows can look a little brutal. This helps explains the horizontal baseline of conventional height. Conversely, the northern elevation is continually in shade and facing 14,000 ft mountain views - so he added clerestory windows to increase northern light entering the building and help balance interior illumination.... but, they are not simply rectangular - they follow the angled ridge line (picture attached). From inside the property these trapezoidal clerestory windows are a key feature to the room and along with the increasing hight adds subtle interest, grandeur and style that sympathises with the mountain views beyond - perhaps this would not be so effective with a more conventional 'simple' shed roof, partly used here to keep construction and maintenance costs low without appearing 'cheap'.