I wish I knew there was a training staff!! Most Plebes in my class did not know this! When they say "Plebe Summer never ends", they are right. It really doesn't end until Herndon, and I never understood why Herndon was such a big deal until now. It wouldn't have made much a difference when applying, but it might have helped me prepare mentally.
I also wish I prepared to follow bad leaders. Adult leadership is not involved unless its admin related. Overall, its kids training kids. The detailers, upperclassmen, and training staff are most likely going to be very new to leadership positions at the Academy. Don't expect great leadership from every single person. There are always problematic leaders, but what is important is that you learn how NOT to lead from them.
I wish I had a little more fun and saved more money before coming here. I saved up a good amount for this year, but others did not and they are struggling! Even though everything is free here, you'd be surprised how fast $125 leaves your pocket every 30 days.