I will comment on only two aspects of this thread.
As far as the "rough sailor" notion goes, take it with a grain of salt but don't disregard it. KP is not a place for the fragile or easily offended. If you can't laugh at yourself, take criticism, endure temporary setbacks, or tolerate the sometimes uncouth behavior of others, you might have difficulty here. Brashness, profanity, and the occasional bout of sexism (almost always in jest, but nonetheless) are common. KP has a culture all its own, as well as a dark, cynical, and no-holds-barred sense of humor that would surprise anyone not familiar with it but is totally accepted and even embraced here. It requires a bit of fortitude and ability to take-it-and-throw-it-back, for lack of a better term. Nobody's going to coddle you, but if you can live in the system you will form incredibly tight bonds with your classmates. Realize also that you will be in a numerically highly male-dominated environment (10:1), and that also has it's own sort of culture. I'm pretty sure that's lower than every other Academy. However, because of the way classmates look out for each other, I would wager that Kings Point is a whole lot safer for someone entering the collegiate environment than most colleges, provided that you're not mortally wounded by having your feelings hurt.
Sea year is different but the same. You will be in essentially a semi-industrial environment and will be expected to pull your own weight. If you don't, don't expect anyone to be gentle about telling you so. Even if you do, don't expect a lot of praise and don't be surprised if you get told how to do it better. You will have to prove yourself as a useful member of the crew. And again, you'll be in a male-dominated industry while you're on sea year, even if that's not where you intend to end up.
Regarding the cross-commissioning: there's two things I'll say. First is that, even though you can come here fully intending on going into the Air Force, remember that the reason that you are here is to be trained as a Merchant Mariner. The taxpayers are sending you here for that purpose, and unless you're willing to spend 4 years learning a trade that you don't intent to use, and learning it to the best of your abilities, then you're somewhat wasting that money. If you can learn to be the best merchant marine officer there is, while at the same time learning how to be an effective active duty officer in the Air Force, by all means come to Kings Point. If not, I can't in good conscience advise it. Secondly, as many of my classmates recently found out, just because KP offers the OPTION of satisfying your service commitment by cross commissioning, does not mean YOU will be able to do it. It is by no means a guarantee that you will get the billet you want, or will be accepted into your desired service at all. This year, for example, while Air Force spots were granted, no flight spots were offered. For Coast Guard, only one flight spot was awarded, and only four spots otherwise. Navy, there were some people who didn't even get Surface Warfare spots, which are traditionally pretty easy to get. Marine Corp and Army spots were likewise picky. So, while there are many options... you might find that in the end, it's not as easy as picking fruit off a tree. Under no circumstances should you come here if you will be unhappy sailing as a merchant marine officer should your active duty dreams fall through.
I hope this sheds some light on what can sometimes be nebulous topics. Best of luck with your choice, and remember: this is the start of YOUR life, not your Dad's. I personally think there is something wrong with any parent that wouldn't be proud of their child going to ANY service academy, but, that said, I'm not a parent. Either way, it's time to make your own choices.