Don't got to college for you're pilot quals. I wouldn't pursue the military unless there is no way to pay for your ratings.

You're 28. You could have all your ratings by 30. Eighteen months CFI then get on with a regional. Two years at a regional at you'd be at the bottom end of the hiring qualifications envelope. You'd be 34. 2022. About the peak of the airline retirement wave. Great odds of being hired by 37. At a regional you'd probably have 5000 hrs TT and have upgraded. At aa AA WO the timeline to transition to AA could be estimated. You can apply to any other airline in that time.

If you got hired at AA at 37 you'd retire around #540 if you got hired today. Hired at 40 today would retire about #850. That will change by the time you get hired and probably for the worse. That's a large w/b line holder. Monthly value of over $30,000. That's what indecision or delays will cost you.

Going to a four year college, instead of straight to a flight school for your ratings, will cost you about 30 months, or roughly a million dollars, at the end of your career. That's why guys are saying 'skip going to Riddle'.