If you want to do a civil ceremony it's hardly an issue.
However, if you want to have a ceremony and a reception back home with all your friends and family, that's tougher to accomplish.
Basically, the Navy wants all of our sailors to request to get married. I know that sounds silly, but there's good reason for it. Mainly, it's so we can tell them what to expect out of their time at A-School, Power School, and Prototype.
Once he lets his chain of command know and they talk to him about it, they'll say yes. But if you guys want to get married in some location that's more than a weekend's trip away (and take a honeymoon thereafter), he'll have to get a leave request in along with his marriage request. Granting sailor's leave during A-School is tricky, but it has been done in the past. He may just get held up until the next month's class-up date.
If you can get everything set up before his current class-up date, it should be a non-issue.
Once you actually are married, it's easy to get into married housing. Well, the last I heard it was. Once again, have him talk to his Chief or Leading Petty Officer, and they'll get him the facts.
Hope this helps. Post any other questions you have or e-mail me directly.
-Jim
EM1(SS), Currently an instructor at prototype in Ballston Spa, NY