As a 30 year old who spend 8 years in the military, he should be eligible for the Post 9/11 GI Bill assuming honorable discharge. This will pay for tuition and fees and provides a housing and book stipend.
If he does not have a HS diploma or GED he may have to obtain it prior but for most this is not difficult. Then he can opt to go down a vocational or more academic-four year route. With the housing stipend coming in, he may feel like he is contributing more and is self improving at the same time. This will also give him some disposable income of his own so he doesn't feel like he's asking for an allowance.
I believe there is a 15 year window to use the GI after leaving the military so do not let it go to waste! This isn't for everyone, heck, he may HATE the idea, but it will give him an option to do something he is good at and/or enjoys.
I'll stay mum on all the other issues as I think it's been covered. Good luck and I hope everything works out for the best.

Mine has the focus of a gnat.
