I don't know about a JAG, but he definitely should talk to someone about the issues of the impact on his USAF career if he has bonds of affection (marriage or otherwise) with a non-US citizen.
If your intent is to marry and live in the US, you most likely should start the proper paperwork to do that. If you are SURE that's the course you want to go, then there's no advantage (and you don't want to incur the delay) of waiting until you're out of student visa to get started.

