usna1985-
In regards to your questions about the negativity, it's hard to explain where exactly it breeds from, but it is certainly prevalent. For my English class, we all had to write a paper on how the academy has changed in our eyes compared to how we pictured it before coming here. After turning in the paper, someone asked the teacher (a Marine Corps Captain) if he had ever had a paper where the author said their opinions had improved... and he responded with a no.
From what I've seen, the 3 major reasons people are disappointed with the academy are because 1) not everybody is as smart as they expected 2) not everybody is as physically fit/tough as they expected or 3) they find the rules rather excessive, and find it hard to think of good reasons why they should go through all this crap when they could do ROTC or OCS.
From what I've seen though, us Plebes generally admit that we are biased because we are currently in the crappy part of the process, and tell the kids here for the CVW that it's really not that bad -- you just have to focus on what the future has in store.
And to subvet-- yes we still climb Herndon, with grease.
My DD is currently a drag at the CVW. Am hoping that she gets the straight-up report from her Plebe and company contacts, complete with all the negatives you share above, the positives that she has long held dear since NASS, and your tempered views of how to try to put things into perspective. The point of the visit, as we understood it, was to help her make an informed decision, but that is obviously a lot to pack into a 40-hour stay under what are obviously somewhat-contrived circumstances.
Thanks so much for stating what you did in such a forthright fashion. It certainly does sound like you are writing from the "dark ages." Hang in there!