Osborne has been published widely over the last two decades. He has written four books on the Depression era and state parks - We Can Take It! The Roosevelt Tree Army at High Point State Park 1933-1941, Images of America Series: High Point State Park and the Civilian Conservation Corps, Images of America: Hacklebarney and Voorhees State Parks (New Jersey) and Images of America: Promised Land State Park (Pennsylvania).

Osborne co-authored with Mark Hendrickson and Jon Inners, So Many Brave Men: A History of the Battle at Minisink Ford which was considered for the George Washington Book Prize in 2011. Between 2012 and 2014 he wrote a comprehensive two-volume, twelve-hundred-page history of the state parks at Washington Crossing along the Delaware River. They were commissioned by the late William Farkas, president of Yardley Press of Yardley, Pennsylvania, and are entitled Where Washington Once Led: A History of New Jersey’s Washington Crossing State Park and No Spot In This Far Land Is More Immortalized: A History of Pennsylvania’s Washington Crossing Historic Park. They will be an important resource for park historians and students of the famed Christmas Crossing of 1776 for many years to come and both books were the recipient of the prestigious Ann Hawkes Hutton Park Ambassador Award in 2017.

In early 2016 he finished writing the first institutional history of the Commonwealth of Pennsylvania’s official railroad museum. The book is entitled The Trains of Our Memory: A History of the Railroad Museum of Pennsylvania 1965-2015. Osborne completed a two-volume history of the Five Mile Woods Preserve in Lower Makefield Township, Pennsylvania in 2017. The books are entitled The Five Mile Woods Preserve: A History and Images of the Five Mile Woods Preserve and were commissioned by Preserve founder Donald Formigli. Presently he has recently finished a new about Robert Henri, the famed international artist who lived in Nebraska. It is now available for purchase.

Osborne was the Executive Director of the Minisink Valley Historical Society in Port Jervis, New York, from 1981-2009 and the Port Jervis City Historian from 1989-2003. During his directorship at the Society, he was responsible for the Society’s Fort Decker Museum of History, and the interpretation of its long and eventful history which included the fort’s destruction during British Indian Department Captain Joseph Brant’s raid into the Minisink region in 1779. Osborne then served as the Curator of Education and Special Events at the Red Mill Museum Village in Clinton, New Jersey from 2010-11.

In 2012, he began a new career as a full-time writer and independent historian. Then, in 2018, he began as the Executive Director of the Robert Henri Museum and Art Gallery in Cozad, Nebraska. The museum manages the largest collection of Henri paintings and sketches on display in the country. There he created four new major exhibits on Henri and coordinated the first national conference on Henri ever undertaken in Nebraska. The museum is presently engaged in building a four-million-dollar gallery that will expand the museum's exhibition space from nine hundred square feet to five thousand square feet.

He has also served on the board of directors of the Depot Preservation Society, Port Jervis Centennial Committee, Orange County His­torical Society (Secretary), the Grey Towers Heritage Association (Treasurer), the Delaware and Hud­son Transportation Heritage Council (Treasurer), the Upper Delaware Scenic Byway (Original incorporator and Treasurer) and the Unitarian-Universalist Fellowship of Sussex County, New Jersey (Webmaster).  He also served on the Cozad 150 committee and the board of directors of the Haymaker Creative District in Cozad.

He lives in Red Cloud, Nebraska, and owns the Wild Horse Creek Company. The mission of his company is to provide exciting journeys of discovery into our nation’s history through presentations, lectures, demon­strations, motor coach tours, and publications. The Wild Horse Creek Company has been providing programs to civic, historical, fraternal, and church groups, seminars, meetings, Elderhostel and Road Scholar programs for forty years.