Wow Corey, you have some catchin up to do. But, you're on here asking questions from the right people, so I will give you some credit for that.
Own room? I think not. In our Squadron of 502 people, 11 people have their own room and there are about 130 officers in the Squadron. Only commanders and field grade officers have their own room (I am on the ground in Iraq). But, we are lucky. A lot of people here in Iraq and especially Kuwait live in large tents with 250 of their best friends, on a cot that is 2 feet from another cot on every side - privates and colonels. I cant say I know all the rules of the Navy, but I do know that a good friend of mine that is an O-4 in the Navy has always had a roommate on deployments on the ships.
As for having a crew: I fly the Kiowa, which is a two-pilot attack-recon helicopter. Everything is a trade off. Sure, we could see a little more if we had people in the back, but then we would have to have a larger helicopter which would mean a larger engine which would mean louder noises - hard to sneak up on the bad guys. But, we dont have seats so its a non-issue. We just have avionics and weapons in the back.
As for the crew chiefs: even attack helos have crew chiefs. I have my crew chief's name on the front of my helicopter. In every type of airframe you interact extensively with the guys and gals that fix the birds, whether they fly with you or not.
As for going out to bars...what an odd question. I am curious why you ask. If you are thinking about joining the Army or Navy as a crew chief to find yourself a hot pilot chick then hey, thats understandable...we're irresistable.
I sum it up like this: I drink with all ranks. I get drunk with officers of the same rank. My career has been safe thus far.