- Is he ready?
- What would he study?
- Is he willing and able to tackle the application process?
- What size of institution will make him feel more comfortable? Big or small?
- How will he handle the fact that he will be a mature student in a sea of 18 to 22 year olds? A smaller college might be more to his liking, but there will be fewer people his own age. How can he overcome loneliness?
Eventually, something's gotta give.