The court does not use the Objective Intent test

The court does not use--and does not even mention--the Objective Intent test. To see why, ask yourself what whether a reasonable person would think this provision

The said George D. Morse shall and will pay to the said trustee in trust for his said minor son Richard the sum of twelve hundred dollars ($ 1,200) per year, payable in equal monthly installments on the first day of each month until the entrance of Richard D. Morse into some college, university or higher institution of learning beyond the completion of the high school grades, and thereupon, instead of said payments, amounting to twelve hundred dollars ($ 1,200) yearly, he shall and will then pay to the trustee payments in the sum of twenty-two hundred dollars ($ 2,200) per year for a period of said higher education but not more than four years'

means George has to pay while Richard is in the army.

It means George has to pay.

It could mean that, or you could also interpret it as meaning George does not have to pay.