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Joe D.As usual, you post something amazing.
The Indian Motorcycle ad looks as though it spelled Motocycle (no R)
which puts it at 1923 or later
http://www.indianmotorcycle.com/ (click on history, then click 1920-29).
Looks like you have a big Durham Bull in the outfield. Wonder what that was for?
Other than that - no other clues jump out at me... but I will look at it some more tonight.