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winter months of 1913 and 1914. 
Returning to Hammondsport in March, 1912 Simon continued as mechanic for Morris. During June both men were sent to the Curtiss Camp at North Island, San Diego, California, to conduct tests on a new Curtiss military tractor biplane, which after further development became the celebrated World War I "Jenny." Simon remained at North Island through the 1915 season on this project then signed up for a flying course in the winter class at the Curtiss School, North Island, San Diego, California. There his instructor was James M. Johnson. On April 5, 1916 Simon obtained pilot license No. 452. 
Following this, Simon was immediately appointed instructor of the Aviation Corps of the Rhode Island Naval Militia, where he remained until April, 1917, when he answered the call for government flying instructors, starting in this service at Essington Field, Philadelphia, Pennsylvania. Also instructing there were Walter Johnson, Harry M. Jones, Frank Mills, Terah T. Maroney and Earl Beers. During the late fall months of 1917 operations were transferred to Gerstner Field, Lake Charles, Louisiana. There, in 1918, Simon was advanced from Senior to Chief Instructor, and later was commissioned as First Lieutenant. During 1918 Simon was Chief Instructor at Brooks Field, Instructors School at San Antonio, Texas. After the Armistice he was transferred to Bolling Field, Washington, D.C., as Inspector and Test Pilot, where he remained until leaving the Service in September, 1919.
Simon then joined Sperry Aircraft Corporation, Farmingdale, Long Island, as factory manager and test pilot, and assisted with their many extensive postwar aviation activities. The most notable of these were the aerial torpedo and automatic pilot, the amphibious flying boat, the development and extensive demonstration program of the Verville-Sperry Messenger, and later the Verville-Sperry Racer which incorporated many novel and advanced features for its time. Simon's contributions on the aerial torpedo and automatic pilot program were especially noteworthy.