Following his schooling in Allegheny City, Osterling began work in the office of Joseph Stillburg, and was published in American Architect and Building News at age 18.

According to Martin Aurand, Architecture Librarian at Carnegie Mellon University in Pittsburgh,[2] Osterling's practice faltered after controversy relating to his anticipated alteration to the landmark H.H.

Richardson Allegheny County Courthouse and a public lawsuit filed by the industrialist Henry Clay Frick.

Osterling's studio was in a building he designed himself in 1917 at 228 Isabella Street in Pittsburgh's North Shore neighborhood.

These plates include views of the Washington County, Pennsylvania Court House, its portico and law library; the entrance and smoking room of the Syria Temple (Pittsburgh); and the residences H.H.