After high school

This is something you would want to confirm with a recruiter but I don't think the Air Force will help pay for college if you go there and then enlist. If that isn't something that concerns you then I would suggest college then military only because I think you'd be able to pay off your loans at an OK rate since most of your needs would be met by the Air Force. If you go Army or Navy they will help pay for tuition if you enlist after your graduate so something to consider.

However, if you want the Air Force to pay for your college then you will need to enlist first and either go to college simultaneously or after you are done in the service. You could also consider Air Force ROTC but you would graduate as an officer and it doesn't sound like you want that. A program like that though will pay for your school as you go and before you enlist.

As I mentioned though, I would confirm this with a recruiter as they are most likely more informed on the matter and intricacies involved.

I don't think I can, but a follow-up question, do you think it is wiser to physically go to college and then enlist or enlist first and do college along the way?