Yes and No. As the height of freight cars increased, ( think hi - cube boxcars & enclosed auto racks ), the value of even a tall cupola caboose diminished. This is why some railroads switched to bay window - type cabooses. Also, a side view of the train was considered more valuable in terms of detecting shifted loads, dragging equipment or sticking brakes. A bay window caboose was also safer for the train crew, in that they didn't have to worry about falling down from the cupola due to slack action or long naps !!!