I was a third timer (which means you usually have 2 years of college but you have applied 3 times) and I now realize what a huge help it was. I was not an academic whiz either at Civilian U or USNA and by that I mean that I had to study hard for everything----nothing came easy. Plebe Year academics were a breeze as a result and it was a good thing as I had, as they say, a "vigorous" Plebe year in Mother B. Youngster and Second Class academics were the buzz saw that humbled me but I knew by that time how to study and how to set priorities so while the Academic Monster didn't eat me, it chewed my tush a few times.
I never have regretted those 2 years as I matured, learned how to study, and was thoroughly disenchanted with civilian universities. My roommate used to complain about how screwed up USNA was and how he regretted not attending a "real" university. I buried him with stories of huge classrooms and being taught by televison, never seeing a prof in front of the class---only his grad students, not getting the classes you need at registration, having to take classes during the summer and having to quit a job to do it, watching your savings bleed away as you frantically try to line up a summer job when you should be studying or taking exams, having profs who never knew you (try getting a recommendation out of them!), being surrounded by stunning coeds and being too broke to do anything about it except look. I had more of social life at Navy than I ever did at Civ U. He never believed me.