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In addition, I also think ill be physically behind because I haven't conditioned hard since I was in high school. Before I contact my areas OSO I would appreciate any advice on what to expect in regards to other candidates experience/ knowledge. Also, how often, if at all, would my OSO help me train or condition before I go (if I get accepted)?
If you are going to become an Officer of Marines, do you really need your OSO around to make sure you do your workouts? You'll have to be self disciplined enough to manage your own workout program. Find a PT buddy and get to it. The OSO may come and run with you from time to time, but he / she is a busy person, and you're just one of many potential officer candidates across a significant geographical area that he is dealing with.