John, when I was growing up, there was an old fellow down the road who had an Indian very similar to the one in your photo. I can't remember the year but he said he bought it when he was 19 or 20. He would have been my grandfather's age and grand dad was born in 1897. So 1917/18/19 maybe.
Had that same great big headlamp, acetylene powered I believe. Had tires of white rubber, the drive belt was made of loops of riveted leather. When I was in my early teens he was in his mid 70's. A couple times a year he would pull it out of his shed, get it going. He would then put on a leather jacket, leather helmet, old eisenglass goggles, cavalry style knee high boots, and a pair of those balloon looking riding pants, and go for a spin. Quite a sight. He was about 6'4" and about 160 lbs. HIs missus never accompainied him though. His break neck travels at 45 MPH were more than she could stand. she prefered the more dignified transit in their 41 Pontiac.