At a young age, Dobson's family moved from North Carolina to Germany; his father had spent the latter part of World War II in a POW camp and had grown adjusted to German hospitality. The Dobson family returned to the United States in 1960, five years later. Dobson later lived in Decatur, Alabama, he felt that he did not fit in well in the South. “I still can’t play a Civil War game to this day.” Having trouble in school, and having had enough of the Deep South, he moved back to Charlotte for college. During college, he was temporarily employed as a faculty member teaching freshman composition and science fiction. Dobson graduated from the University of North Carolina at Charlotte with bachelors degree with an English/writing major.

Out of school, Dobson soon worked three jobs: a temporary typist, substitute teacher, and a planetarium operator on weekends. “I worked real hard to get a real job,” explained Dobson, “and I was finally hired as a research assistant in the Aeronautics Department of the National Air and Space Museum of the Smithsonian Institute in Washington, D.C. It was a great first job!” In 1976, Dobson began overseeing the business operations of the Albert Einstein Spacearium at the Smithsonian, and then running a résumé business in 1979. Dobson was hired as an editor at TSR, Inc. in December 1983, and moved to Lake Geneva, Wisconsin with his fiance Debbie Singer, whom he had met in the resume business; they married on the Fourth of July in 1984. “The first three projects I worked on at TSR never appeared in print,” recalls Dobson. “I got a special satisfaction out of editing wargames. They were tough, but I loved the preciseness and detail.” The projects he edited included the Dragonlance series, as well as the Battlesystem fantasy combat supplement, which won the H.G. Wells Award at the 1986 Origins Game Fair. In 1985, Dobson was asked to join the Marketing Department and ended up as Marketing Manager. In March 1986, Dobson became the Director of the Games Development. As a game designer, his credits included the four-module AD&D-game Bloodstone Pass series with Douglas Niles, and X10, Red Arrow, Black Shield, both of which involved the Battlesystem rules; Dobson also co-designed the Partyzone Knave of Hearts game with Debbie. Dobson switched fields yet again to become a seminar leader in 1990, with authorship of several management books, tapes and videos to his credit. The publication of Fox on the Rhine in 2000 marked the beginnings of Dobson's forays into Alternate History.

In his RPG and Alternate History books he has frequently collaborated with Douglas Niles.

Alternate history

Fox series

• Fox on the Rhine (2000) with Douglas Niles
• Fox at the Front (2003) with Douglas Niles

non-series novels

• A Novel of the Invasion of Japan (2007) with Douglas Niles