Nice video, thanks for sharing it.
I think I've seen a real pilot wearing an IWC about once over the years. Just as it could be argued that we are not really pilots as in the old days, I would say that a watch with a variant of the common ETA Valjoux 7750 movement could not be called a classic mechanical chronograph. But, times change, right?
Looks like the hotel is the familiar Copley Plaza in BOS, I've had a layover or two there in years past. Never bought a watch though.