For right now, I don't see the reasons for your anxiety, concern or fear to keeping all your and his options open. Right now.. you have atleast 2 more years of school... He can reup (reinlist) for another two years... There is a REAL GOOD chance as you both 'grow' explore, and allow more time to solidify your thinking, get more information, etc. you will BOTH be in a better position to know the best decision for each and/or both of you.
What I am hearing is LOTS OF FEAR... which usually leads to a greater NEED TO CONTROL... either yourselves or the other person. Whether you don't want to be away from each other or fear lossing each other.. you both will continue to struggle with what each of you want and what 'the other person' wants. STOP THE ANXIETY... Where is the Trust? I assume you both have SOME LEVEL of trust in yourselves and in each other. NOONE KNOWS THE FUTURE or What your thinking will be two years from now.. Hense, take the pressure off to MAKE A DECISION.. rather, allow time to 'brain-storm' the various possibilities.. That CAN BE fun.. or it can be scarey if you're insecure. Bottom line, if either you or he or both are insecure.. you will have LOTS OF PROBLEMS with ALL THE MAJOE DECISIONS in your lives. At the very least, it sounds like you both need more TIME, NOT more PRESSURE to force a decision about what to do two years from now when you get out of school. In the mean time, he can reup or leave or pursue school or whatever. that is HIS Decision... it IS HIS LIFE. You already have a committment for the next two years.. It is HIM that doesn't know what he wants in the next couple of months or whatever when he has to make a decision about staying in or leaving the military.
It also sounds like you 'get upset' when he does consider options that you may not like.. THATS NOT LOVE...thats POSSESSIVENESS... Are you that insecure?? and are you not trying to ultimately CONTROL HIM?? Is that FAIR and will that be the bases of all future decisions?