Reddit mentions of My War: Killing Time in Iraq

You don't have to worry about how to write it, just get it down and out of your brain onto paper. The technical stuff is what editors get paid for.

Also, try reading books about other interesting stories. They don't necessarily have to be on the same topic. Creative Non-Fiction is a huge genre right now, and it sounds like you have tons of material to work with. Don't worry about being super strict with the details, unless you decide you want to be. It's the story that's interesting.

Suggested reading...

• Jack Kerouac: On The Road - I'm not going to give you a link because you should have this on your shelf already, damn it! :P
  
• Colby Buzzell: My War (side note, I followed this guys blog as he was living this story and it was mind blowing. The only blog I have ever followed.)
  
• Gregory David Roberts: Shantaram - I'm reading this right now and it's spectacular. I think you might appreciate the themes, as well.
  
  I'm sure other redditors can flood you with even more suggestions.

Assuming you're asking about life in the military, and not specifically West Point, it varies greatly with rank, duty station, and military occupational specialty. I suppose the short version is expect a more desk-like environment if you have a Combat Support or Combat Service Support job, versus a lot more time "in the field" for a Combat Arms job, and an overall better or worse quality of life depending on where you are stationed (both because of the mentality of units there and what the area is like).

There are a lot of autobiographical books by soldiers that have come out over the past decade that you can check out. Most of them will of course focus on their deployment, but it's common to see a bit of the training. I haven't looked into that category of books in years, but as an example, one that I read when I was younger was My War: Killing Time in Iraq, by Colby Buzzell. Just remember that with any autobiographical work, the author is limited by what their point of view was. In Mr Buzzell's case, as a lower enlisted soldier he was right where "the rubber meets the road", but didn't have much of the bigger picture (also, I have never heard of a unit that did training quite the way his did).

I wouldn't worry about fitting in because of where you come from - no one really cares where you're from, plus I know quite a few people who grew up in the liberal bastions of America and did alright in the Army.