In the Navy I was offered Annapolis in boot camp because of one of the test scores. Didn't do it since I was engaged and I got a pretty good gig anyway.
We make choices but we should have no regrets about them. Always, at the time, they were the right thing to do.
I enlisted in 61 and served exactly three years. Most of the guys I remember were draftees. They were the backbone of the Army, and many times, they seemed to be watching the rest of us grow up. Just as I was growing up my three year enlistment was up, and had not considered reenlisting. My commo platoon leader, a fine 1LT tried to talk me into applying for OCS. I declined.
I was out a little less than a year, working and taking some college courses. One day, my younger brother wanted me to accompany him to the recruiter's office in Jackson, MI. He wanted me there so he would get the straight skinny on enlisting and then going to OCS (as if I knew the straight skinny). While there, I asked the recruiter about Flight School for someone with prior service. He checked the regs and told me he'd give me a bus ticket to Detroit to take the test. If I was accepted I'd have to reenlist for two years. If I made it through flight school I'd owe them three years.
Two tours in Vietnam and 18 years later I retired from the Army. I took a direct commission like a lot of warrant officer aviators did in the late sixties. Other than getting to command a basic training company, there were times I regretted taking a commission, but 'pushing troops' was more than enough to make it right.
Oh, my brother did go through basic and Armor OCS. He served two years and has always regretted getting out.