I live in Norfolk, have lived here (except for active Army service) since 1954 when my Navy father was transferred here. The Norfolk Naval complex is the largest military installation in the free world, so I would have to know exactly where your son will be located on it to know what rental property is near him.
There are off-station military housing located just outside the Naval Station, Naval Air Station, Navy Amphibious Base, and Naval Support Activity. There are civilian rental properties located all over Norfolk that welcom military personnel, many within bicycle range, much less Jeep range, of the various Naval installations.
I believe that you also mentioned educational institutions. Old Dominion University (my alma mater) is a few miles north of the Naval Station Main Gate on Hampton Blvd. There are numerous schools that teach extension courses on base (how I earned my Master's) and at various locations in town.
As for off-roading in the area, I am afraid that (except for military duty) I cannot help -- I have had my Jeep for only three days and have just joined WF to find off-roading opportunities myself.
Please contact me directly if you wish me to develop more specific data on rental or educational opportunities for your son.
Dien Cai Dau