While The Elgin Academy had a stellar reputation as an educational institute, its ability to economically sustain itself was not always apparent.  In fact, E. C. Alft writes, "The Academy's fortunes have resembled a...movie...called 'The Perils of Pauline'.  Each episode would end with the heroine in dire straits, only to be rescued...in the next installment".  Throughout its life, The Academy would be faced with possible closures due to the lack of money almost every year it was opened.

Under Amos Sears, the school would know some economic stability.  From 1870 to 1881, Sears organized a curriculum designed to stimulate students in the areas of "College, Teaching, Business and Life".  During that time, attendance would swell to as many as 300 students and the school would enjoy a period of  prosperity.  

Judge Nathaniel C. Sears, son of Amos, and Nathaniel's wife, Laura Davidson would continue in the legacy.  Davidson was the granddaughter of James Gifford and both were alumna of The Elgin Academy.  In 1924, a series of gifts from the couple would convert the physical plant, build a new gymnasium and build new dormitories.  Included in their donations was The Laura Davidson Sears Academy of Fine Arts, which houses a collection of fine painting that the couple acquired.