Mom of plebe here--you are going to find that the answers to your questions will vary greatly depending on who's responding. I belong to a parent FB group for 2016, and the experience is different for each mid. As for mine......
1. Reality--what he expected to be hard turned out to be easy, what he didn't anticipate turned out to be difficult.
2. Harder--he's an introvert, so PS was tough because he was around peers 24/7--no time to recharge. He was also disappointed that some of his peers were "slackers"--not the caliber he expected at the academy.
3. Easier--the physical requirements of PS--not nearly as tough as had been advertised. The AC year--classes are going well.
4. Miss--freedom to do as you please, friends, pets....
5. Didn't miss--hmmm, access to electronics and media entertainment.
6. His company allowed the plebes to choose their own roommates after PS. He opted to room with someone who was having a difficult time finding a roommate--turned out to be a good decision as his roommate's "quirks" don't bother him and they are on the same page about room cleanliness, etc. (Other roommate situations have not worked quite as well, as would be expected in any "dorm" situation.)
7. He likes the food well enough, but misses home cooking. (We ate in King's Hall last week with him.) Lots of choices, fresh fruit, milk and salad available; main meals tend to be greasy.
8. Validated classes--a year of French, calc, honors English (not a validation, just a different placement), 1 semester of physics, hopefully swimming next semester. Has worked well so far, will allow for some flexibility later on.
9. Not apt to go into town--remember the introvert part--would rather spend time with his sponsor family, complete school work or email/catch up with people/family. Annapolis is small, so there isn't a whole lot of choice once you've been out and about.
10. Phenomenal sponsor family--not always the case for everyone.
11. Letters, care package--but not too many of the latter, limited space and plenty of food at King's Hall--again this varies greatly mid to mid. Some parents send monthly care packages or more, mine has asked that we limit what and how many we send.
12. You can go to away games if you put in a chit. Plebes are low man on the totem pole, so they sign up last. Travel is reimbursed up to a certain amount. (If grades are unsat, restrictions will be in place, so there will not be Saturday liberty or away football games.)
13. My plebe has always been very careful with money, so he's not spending much. He'll buy what he needs at the mid store; replaced his broken alarm clock, school supplies, etc. We have sent him no money--he says he doesn't need it. Other parents are sending money on a monthly basis--again, depends on your buying habits.
14. Academics are the main reason plebes struggle. Some haven't had the background (chemistry is called the "Plebe Killer"---has gone well for my plebe, but he had AP chem in HS), but often times it appears to be a time management issue--lots of things to learn in lots of classes. A couple of classes require lots of memorization, 3 have papers that need to be written, 2 have homework problems to be completed and plebes are expected to complete more problems on their own if they need the practice. Add to that the required physical training, and lots of other "plebe only" practices--chow calls, hallway restrictions, professional knowledge quizzes administered by the 2nd class, signatures to obtain, boards to decorate, chopping everywhere in Bancroft---it gets to be very wearing. Then there are the mandatory football game attendances, parades and practice for parades, duty, briefs, company PT--you get the picture. Limited time, so time management is critical for success.
15. Wish that he'd been told-- Goes back to his main disappointment--peers are not always doing what they can or should be doing and their actions impact the group. Philosophically speaking, people will be people everywhere. Some of the mids play well with others and meet the expectations of the upperclassmen and the academy, others do not. Don't expect everyone to take it seriously or pull their weight. No matter how well prepared you think you are, expect an unexpected reaction from yourself. The fatigue, the constant grind, the additional plebe punishments/restrictions can really wear on the psyche. Take the long view and remember, "to eat the elephant, take one bite at a time".