The first 4 years (the scholastic time) is the toughest because it's such a big adjustment. Then he'll have 4 more years when no one will really respect him because he'll be given a title based on going to school and will be in charge of men with a million times more experience. If he keeps his mouth shut and his eyes and ears open, he'll be a much better person for the experience and far, far ahead of anyone who just went to college and then off to a job for 4 years.
I don't know about that. It's pretty easy to meet people outside the military and chics totally dig the uniform. The reason "military-to-military" marriages are more normal is because people around the same age who're both serving tend to understand the sacrifices and are far more mature than their civilian counterparts.
When I was 21 years old I had 15 people working for me and was in charge of over $60,000,000.00 worth of equipment, just to give you a frame of reference.