Sir, I read both of his posts a couple times, and I don't quite see it the same way you do. He was talking about his future wife or girlfriend working on base (as an RN). I am assuming he was asking about retirement for her if she were to work a full 20 years (which she would have earned).
As far as him transferring his G.I. Bill to her (which he would be allowed to do if they were married under the new G.I. Bill), that wouldn't be freeloading either. If he did X many years of military service and paid into his G.I. Bill, it would be his to use as he pleased.
I don't think he's trying to suckle at the proverbial taxpayer 'tit' here. I think he's just getting some information to help him make an informed decision.
If his intentions aren't true to the cause, OCS will filter him out in a heart beat.
My humble opinion anyhow...