Here are my 2 cents on this:
You sound very prepared and determined (as well as very motivated). Those are excellent attributes. Very admirable. Go for it, if you want!
But keep in mind: many things are easier said than done, and this won't be easy no matter how much you plan ahead. Even the best laid plans don't manifest the way we want them too.
I am the co-founder of a local non-profit theatre company here in town (a friend and directing graduate from Columbia College in Chicago and I produced a production with our high school alumni from a span of graduating classes. We later registered as a state of Michigan non-profit organization and have produced shows and cabarets since). We functioned: director, stage managers, marketing, set design, producers. The only money we had was what was donated from our former high school's drama club for the rights to a show we were producing. We later paid the fee back and made a small profit. Everything else was either donations or we raised the money on our own.
We made it work, but we hit every obstacle you could imagine! Before, during and after production.
Additionally, I've also directed at the high school level for a school that really didn't have funding or support. Therefore, other tasks fell on our shoulders as well... play selection, set building, fundraising, directing, SMing...(or training the SM student).
And again, obstacles.
We overcame them. I learned A LOT from these experiences, but it's also easy to burn out.
Just know that advice comes from a good and experienced place.
Whatever you choose to do, BEST OF LUCK TO YOU!!!!