Answered all questions, I hope I helped!

I'm very curious to see how the monetary reward works out.

Just as a social and economic matter, it seems to me to be overwhelmingly likely that dropping out of high school will do long term and maybe permanent damage to your ability acquire significant money and free time. Dropping out of high school is very likely to be the worst thing you can do with your life right now. On the other hand, getting straight A's (which is not an intellectually challenging task) is likely to pay off more than anything else you can invest your time in. I'm not saying that that's the way it should be, I'm just saying that that's the way it is.

An hour spent on maximizing your grades in high school is for almost everyone one of the most financially efficient hours you will ever get an opportunity to spend. And you'll need money if you want the independence necessary to make a difference.

Barring some extreme mitigating circumstances, top colleges will throw your application in the trash the moment they see anything but a high school diploma littered with A's. They won't read your writing sample, or your personal statement, and so they won't know about any of your efforts to educate yourself. They do things this way because they get thousands of applications and they need a way to screen out ~70% of them without doing any real work. And if you're white, male, and not attending a well-respected high school, it will take more than good grades, but that will at least get your foot in the door.

Unschooling is great, but if it comes at the expense of the kind of schooling where you get a piece of paper at the end with a bunch of A's on it, then it's very likely to be an economic and social disaster.

So here's my advice: Don't drop out of high school. Get nothing but A's from now on. And spend the rest of your free time learning about what you find most interesting and valuable or hanging out with friends. Learning how to deal with people, both instrumentally and morally, is not a low priority.

Idea for pomodoro technique: try making a 30 minute audio clip that consists of 25 minutes of "pomodoro timer noise" (some noise you condition yourself to concentrate on, e.g. find some waterfall clip or something), then 5 minutes of silence. Then play it on loop. Makes it easier to not get distracted when the timer is running and also ensures that the timer is always restarted. Make rules related to when you can turn off the looping, e.g. if you're done with your homework for the day, or you spend at least 30 seconds writing down reasons to keep it on and decide that you should still turn it off even given those because you're too tired to work effectively or whatever (see also). Maybe also make it give you a warning 30-60 seconds before your 5-minute break is going to end.

Given that you've failed at this so many times before, I'd recommend being extremely strict with yourself this time... really figure out in advance what the rules you'll follow will be, brainstorm cases where you'd want to break them, and either add exceptions and decide to continue following them for every case that you brainstorm, and then be extremely anal about following the rules once you start actually using them. Additionally, probably make the rules pretty reasonable and easy to follow to increase your success odds even more (but still be an extreme stickler about following the rules you do set out; err on the side of following them too well). Also, if you've been failing at doing your homework a lot recently, I'd say give up on trying to do it ahead of time and just deliberately do it at the last minute for a few weeks, so you stop practicing the action of attempting to improve your study habits and failing (it sounds like you've practiced this a lot, and you don't want to just keep practicing it. It's not "practice makes perfect", it's "practice makes permanent".) Have a day planned in advance when you will switch to the new pomodoro productivity scheme you've been working on... September 30, say (that's a Monday, right?)

Why not apply to college right away? Not seeing the need for the 3-year waiting period. You won't have formal qualifications anyway, so either you can convince them you know your stuff, or not.

I think the question depends a lot of the social support that you have. I don't think that an internet forum is enough social support to expect to be really productive while being completely alone.

From there, I go to cross country, taking my time until 6:00 PM at the earliest.

Why?

That seems to be time that you could use otherwise.

I would also add that "cross country" doesn't seem to be a term with a fixed meaning and I can find many things under that label via google.

Huh. Ask Eliezer about that

Eliezer is a profoundly unusual person who has had vastly more success than most people with his level of education.

decades of monotonous work

many people are able to find interesting high paying jobs in the for-profit sector.

especially since there are so many other organizations and individuals who could create an impact thousands or even millions of times more than mine.

This is also an argument for taking the donating money path to helping. Remember, money is a unit of caring.

With those updated plans, which of my three options (or neither of them) are the best?

It depends on your skill set, but I would guess (1) in part because of what your parents think. If you are a computer programming genius (i.e. someone is currently willing to pay you >$100/hour) then perhaps 3.

Having akrasia problems is an argument for staying in a highly structured environment.

But don't you attend school only around 180 days/year (if in the U.S.)?

What's the technique that came closest to succeeding and how specifically did it fail?