He needs to prioritize: what is most important to him? Is it flying? Is it a degree? Is it serving as an officer? The answer to each directs a different approach sometimes.
For example: if he has an engineering degree, and is on an ROTC scholarship...he is set for the AF. If he is PQ at graduation (earlier in reality) and is selected for SUPT, then he goes off the fly. If something happens in SUPT and he doesn't complete the program, the AF sees an engineer with lots of potential for all manner of career fields.
If he has a generic degree and this happens...the AF may have difficulty finding a field for him. He could be voluntold to a career field he is not at all interested in. A classmate of mine from USAFA...military history major. Went to UPT...was burning up the program until he GLOC'd in the T-38. Grounded from that point on as he was unconscious for quite some time (the IP brought the plane back). He had "that degree" so...the AF evaluated where to put him and he became a military security forces officer. For many folks, that's a great field; but for him, he considered he was 50% in hell and was waiting for the final call. He bailed the second he could and went into industry...eventually working his way up to a fine career, but it took time.
I'm all about building the most impressive package possible to make oneself valuable to all. I have a BSME...barely survived it at USAFA. However...when flying didn't work on the outside, I ended up at a computer company designing computers (no mech stuff, just computer geekery) and eventually ended up a "Staff Electrical Engineer" at Motorola. They said they hired me for my USAFA degree, the Mechie part was a bonus and they'd teach me the EE stuff I needed to know. And they did and I loved the job!!! And I was still in the AFRC so...life was pretty good!
In my case, when I didn't get an airline slot (bad timing) I thought I was done. However, the background I had in engineering (school only) and serving as an officer, turned out to be very valued by corporate America.
He needs to think strategically and not tactically.
Just my humble opinion, which, with $1.18 will get you an XL Polar Pop in an AZ Circle K!