My advice? Do what you want and whatever makes you happy. Look for weird, off the path stuff. You are going to be fodder for any board after taking NROTC orders. That my sound harsh, but with the abysmal selection rates in the last few years, you would be chasing a brass ring for nothing but disappointment and I hate it when people blow smoke.
Are you looking to get out and use your Master's on the outside? I would start looking for a job that will network you into something. If the detailer is feeding you the "nothing but the boat" line, just remember that nobody cares about you like you and searching for orders without his help may be the best thing for you.
If you have to go to the boat, ask about staff jobs, aide jobs, etc. Those will give you the best chance to work an angle later on outside your community. Your community is going to do nothing for you from here on out. Don't rely on them to do what is in your best interest. You need to start looking way outside the box...there is some really great stuff out there that you and I have probably never even considered.
Best of luck, and I mean that.