A couple friends of mine took a year off and climbed the Appalachian Trial (the whole thing) by themselves - and in the winter, too! This is an option to consider.
I would look for a fulltime job in a law firm or somewhere your son could get good, solid letters of recommendation. Colleges won't look down their noses at gap years - many people need them to mature after high school. Oh, and be wiser when selecting your schools
