Mid-Career Switch while juggling responsibilities

What's up, you gigachads?

I've been following this website for a few years now. I turn 25 next month and I am going through a bit of a mid 20s crisis. I've worked with some fine startups as a UX designer, failed to move into project management, made several thousands (in the 10s, not 100s) as a sports bettor, and have most recently been working in telesales for tech companies.

I'm ready to stop messing around and pursue a real career in IB, with MC as a fallback. I am prepared to enroll in a community college (cheap, was not the best HS student) that has a transfer program into UNC (target school with a >50% transfer rate). However, my issue is that I currently make $80k in base salary before commission and I have to support myself as well as a loved one. So money is a major concern while going to school full time. I work two sales jobs remotely, so if I dropped my 9-5 then I'd be down to $30k base.

Thus, to circumvent my age, background, and make some extra dough, I am considering going to the Air Guard and having that help with college while also being able to get some extra money (including ADOS). Full list of options are:

• Air ROTC while getting my degree then 4yrs active duty then pursuing IB (8 years)
• Air Guard as an enlisted soldier while getting degree, then pursuing IB (4 years+training)
• Army Guard ROTC (where I can serve as a reserve after graduation, but it's the Army unfort) while getting degree, then pursuing IB (4 years+training)
• Get my degree, then commission into Air Guard as an officer, before pursuing IB (4 years)
• Skip the military altogether and utilize shit like Scholly, community college, etc. while living below my means with the $30k base.

To get into a BB, I do need time and energy to focus on maintaining a >3.75 GPA. Not sure what to do, but would love insight, please. It's been my dream to work in business, and I made some mistakes that I am desperately trying to atone for. This is my last chance in life.