Another entry from 1933, R. M. Abraham's "Diversions and Pastimes" (still available in a Dover version) poses a slightly different approach with this problem from page 16 (problem 61). "A traveller returning to New York found that he had only a ten-dollar postal money order, and that his train fare was seven dollars. The ticket clerk refused to accept the money order, so the traveller went across the road to a pawn shop and pawned it for seven dollars. On his way back to the station he met a friend, who, to save the traveller the trouble of returning to redeem the money order, bought the pawn ticket from him for seven dollars. The traveller then bought his ticket and still had seven dollars when he got to New York. Who made the loss?" David Darling in his "The Universal book of Mathematics", credits this as an earlier version of the three men in a hotel version above.