Co-chair of the DC Reentry Task Force, Louis Sawyer, was featured in this Washington Post article. He spoke of how his family took 14-hour road trips to visit him in federal prison in southwestern Virginia, until he was moved to a prison too far away for them to continue their visits.
The article points out that since DC is not a state its criminal legal system is controlled by the federal government. For example, DC residents who are incarcerated for felonies are sent to federal prisons all over the country. Further, when those people finally come before a parole board, they see a board whose members who have little context for what a return to life in D.C. means.