Dwight David Manfredi was named after Dwight D. Eisenhower ("D" as in David). Eisenhower helped win the Second World War, by leading the offensive in North Africa and Normandy.
The episode title "Go West, Old Man" is a variation of a quote by Horace Greely, editor of the New York Tribune, "Go West, Young Man and grow up with the rest of the country".
Like Dwight, Stallone's father was also a barber/hairdresser and he was also a senior in high school when John F. Kennedy (JFK) was assassinated.
Many of the places shown as being in Tulsa are actually in Oklahoma City (OKC). The Higher Plane is in OKC across from the Farmers Public Market. Bred 2 Buck in actually the Whiskey Barrel Saloon. All of those locations and more aren't filmed in Tulsa but instead in Oklahoma City.
When a person has been institutionalized for long periods of time, they tend to be out of touch with current events and cultural shifts, as demonstrated by Dwight, informally called "prison dumb". At the end of their term, one might be mandated or strongly encouraged to take a "life skills class", before they re-enter society.