Let's start wit the last question first. You don't get "transferred" to the Naval Academy - you get accepted for a scholarship to be a student there. The selection process is rigorous and competitive. You should start This Very Minute!!! if you hope to get in.
Now, let's get to that guarantee crap. They're gonna tell you no. They have absolutely no control over what the Navy's needs will be 18-24 months after they ship you to RTC. You don't have the right to "demand" anything, and you have already signed a contract which you are required by law to fulfill. Sure. you can refuse to sign, or put your hand in your pocket when it is time to take the oath. They have no obligation at that point to drive you home to mommy if you do, so bring bus fare. They will also be pretty tired of you when you come back later asking for another chance to enlist. Who knows, they may discharge you from DEP with a negative recommendation for future enlistment. Try getting into Annapolis after pulling that stunt.
But here's the best thing... thay can give you what you want and send you of smiling to boot camp, only to tell you later that they don't really have to do it 'cause the fine print ALWAYS says that the needs of the Navy come first. Or they can even transfer you to your desired duty station.... and transfer you somewhere else ninety days later.
I think this friend of yours is shining you on a lot more than your recruiters have. If you look back objectively, you'll find that they may have been "artful dodgers" but they never actually told a lie. Your sea-lawyer friend however, is feeding you a line of crap.
Here's the deal... you go into the Navy a boy and come out a man. Better for you if you start making that transformation sooner rather than later. You're not leasing a car, signing up for a gym membership, or picking a college. You are volunteering to serve your country. You are not shopping around to see what your country has to offer you. Other than marriage and parenthood, this is the most serious and binding commitment you will ever make.
Now for the good part. For all the hardship of family separation, bad duty stations, difficult cliving and working conditions, hard work and sacrifice, you will be rewarded with the greatest character-building experience known to mankind. You will acquire skills far beyond technical training. You will learn and practice leadership, decision-making, flexibility, endurance of body and spirit, self-reliance and teamwork. You will be a member of the world's most honored fraternity, and you will have earned the right to do with confidence things that others are too timid to try.
So, go where they send you, do what they tell you and don't end up a whining sack of crap like your moaning, game-playing, sea-lawyering friend.