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One day this summer, a University of Chicago student biking to school was struck by how a sculpture featuring figures holding their heads in exasperation seemed to mirror the mood of many of his college peers, who at the time, were mired in finals week, according to Yuval Degani, president of Dream Town Realty.

Captured by the parallel, he whipped out his smartphone and shot a photo of the angsty figures, Degani said …