I'm not sure they have requirements for SLE, but if you're going into the Army, buzz it off, lol.
Yea no I had long hair too, cuz I played in a band and we all had longerish hair, like a rockstar (ughhh, I look back at that with deep shame...) Now I buzz it down, and IMO it looks better. But, if you go to the Army, they'll make you cut it anyways, so I would just do it now, but I guess you don't have to.
Get it trimmed so it's not sloppy and it'll help maintaining it since you only will have about 10 minutes to get ready each morning. There's no hair "standard" for SLE CC's but keep in mind you are going to a military academy so a well groomed haircut will give yourself a better appearance. Also stay clean shaven.
I am not sure if I want to go to a service academy and hoping that the West Point SLE will provide the experiences that I need to decide.
Getting it at least trimmed and looking neat is a great idea. If I stick with the non-buzz cut hair, is it OK to wear a buff?
The great thing about hair is that it grows back. Get it short enough to be manageable, and if you decide the Army's not for you, it's not like you lost a part of yourself that won't come back. One thing about the Army: it requires sacrifice. Are you willing to part with some of your hair for the opportunity to serve your country?