I'm looking for clues to the identity of the man in the photo so it makes sense to start with the automobile he's in. "If" this is the Yankee Fotographer shown in the image, he died in 1925, so the vehicle is likely from before that.
To me the lines of the car aren't striking, but the grille with the downward-slanted V-configuration strikes me as unique. (Or were guys into customization back then, too? The Yankee Fotographer was a real car-guy of the time, with a 1903-ish Waltham Orient speedster -- thanks nzcarguy for the ID-- a Brush, a 1911 Ford, and a 1918-ish Willys Six.)
What make and possible year come to mind?