Upon completion of his Medical/Surgical training in 1990 he was stationed at Homestead Air Force Base in Florida as a Flight Surgeon and staff Gynecologist. Soon after his arrival at Homestead Air Force Base there was the invasion of Kuwait and the beginning of the first Persian Gulf War and Dr. Osborne found himself being mobilized to the Middle East (Daharan) in November of 1990 as a flight surgeon and the second in command of a MASH unit. In 1991 Dr. Osborne returned states side to do specialized training as a Germ Warfare Officer in support of the war.
In 1997 Dr. Osborne received his MBA from the University of Miami.
Dr. Osborne was appointed a Assistant Professor of Medicine at the University of Miami School of Medicine in 1992, and an Associate Professor of Medicine at Mt. Siani Hospital residency program in Miami Florida in 1993.
Dr. Osborne was the Chairman of the South Florida Perinatal Society from 1992 to 1994 which was responsible for perinatal services for the entire state of Florida. He was also Chairman of the South Florida Healthy Start Program.