What you "SAY" doesn't make sense; but what you "Mean" makes sense. What Sparrow said is correct. Let me break it down in a chronology that will make more sense:
1. High school senior: Apply to academy: medically disqualified
2. Attend civilian college freshman year:
3. While a freshman at civilian school, apply AGAIN for air force academy
4. Medically disqualified again and not selected to the academy
5. Start your Sophomore year at civilian college, apply AGAIN for air force academy.
6. Medically disqualified again and not selected to the academy.
Stir briskly and repeat as needed. Some things to keep in mind.
1. We are "ASSUMING" that the medical disqualification you are referring to is a temporary condition such as a broken bone. If it's something like asthma, then that's NOT temporary, and you will NEVER be accepted, so there's absolutely no reason to keep trying.
2. You can only apply to the academy until you reach your 23rd birthday prior to the end of June. If you reach your 23rd birthday PRIOR to starting basic training for the academy, you are NOT ALLOWED to attend, so once again, there is no reason to continue applying at that point.
3. MOST medical conditions that make you ineligible for the academy, probably make you ineligible for the air force at all. I say "Most", that doesn't mean ALL.
So if you are denied an appointment to the air force academy for medical reasons, you will have to assess the medical reason at the time to determine IF YOU CAN reapply a 2nd, 3rd, or 4th time..... OR, if you're even allowed to go into the air force at all. Even enlisted or after a civilian college and going for a commission to be an officer. In other words, your "Scenario" is too vague with way too many possibilities.
I hope this explains it. If not, someone else can try and explain it, because that's the best that I have. Best of luck.... mike.....