It could well be, that the high-wheeler is a Kearns surrey from roughly between 1911 and 1913. Many details fit, like the rounded hood (not a dummy: it covered a 3 cyl. 2 cycle engine) and the 16 spoke wheels. The angle of the steering column seems flatter than on the images I could find, but I do no have the impression that all images in their adverts were up-to-date. Kearns also had a 'convential' car line, in which the steering column had a similar flat angle, while the outline for the chassis was virtually identical to the high-wheeler, and even the wheels, though with pneumatics, had 16 spokes.