There's a lot to unpack in your question, and I'm a little drunk, but I'll do my best. In addition, I feel like you asked hoping for an honest answer, so I won't feed you any bullshit. I joined the USMC at 27, so age isn't a big issue, but I was also in good physical condition, so keeping up with the younger Marines wasn't a problem. Depending on how "out of shape" you are, this could be a long journey. However, bootcamp is designed to take the average American off the street and turn them into a troop (your mileage may vary based on the branch you join). I believe the Army accepts recruits up to 35 years old. That being said, if you are extremely out of shape, now is the time to start addressing the problem. A few months of dedicated conditioning and responsible eating are enough to get even moderately out-of-shape people to the minimum requirements to ship off to basic. There's no question about it; that much debt may make you entirely ineligible for service. I'd recommend talking to your local recruiter. With recruiting efforts struggling, there may be leniency for people in your position. There may be a waiver available, but $50,000 seems like it may be too high. Depending on the MOS contract you want, there may be no wiggle room at all for debt (especially for higher security clearances). If you get your situation in line and everything works out, you will be able to enlist; it's smooth sailing from there. Keep your nose clean for four years and do your job to the best of your ability. After your contact ends (and as long as you receive an honorable discharge), your benefits will open up. If you maintain enough credits per semester, you will be considered a full-time student. After four years in any branch, college will feel like a joke, no matter how much work professors throw at you. The VA will give you a monthly allowance (BAH) that can be used on housing, groceries, etc. Every GI Bill recipient's BAH is calculated based on the price of living in the county where their college is located. Keep in mind that that allowance is in addition to the GI Bill, which covers all costs associated with normal tuition as well as the required flight labs you will take at a Part 141 flight school (flight labs cost upwards of $200k alone). There are also plenty of grants that prior service members can apply for (specifically the pell grant) that award roughly 3.5k per semester for full-time students (this depends on your income, though). Overall, you can live very comfortably (as long as you don't have dependents) through four years of college, as long as you live within your means. One point that's important to add is that joining the military for college benefits is common. The incentive is there for a reason. But you must realize you are still trying to join a warfighting organization. You need to have that mindset going in. If you're unwilling to throw your name in that hat, then maybe you need to find another path. "Is it too late?" was your first question, but I saved it for last for a reason. Of course it isn't. The debt is going to be your biggest hurdle right now, but I promise the rewards are worth it. So you have plenty of time. This dream is definitely worth it, but you have to make some sacrifices now. If you need anything at all, don't hesitate to reach out. Good luck out there.