From that perspective, your non-profit could be creating the illusion of progress - helping raise the people you work with in belize out of poverty, while simultaneously taking jobs from other, poverty stricken people in EG india.

The nature of wage markets means the jobs would tend to go to the worst-off people who can take the jobs, whose wage demands would be lowest, as they'd have the most to gain from a given wage (that is, they'd take the job for less money, because the money is more valuable to them). This isn't a bad thing, although it's usually presented as one, particularly by those whose wages would be undercut.

(This doesn't consider market barriers or interference, granted; for one example, a mountain village might have the most to gain, but be unable to offer competitive labor pricing owing to the cost of providing infrastructure.)

There's definitely a market there - as you clearly are aware (from mentioning upwork) there's a booming market in these types of remote work arbitrage opportunities.

I'm curious what you expect your value to be over and above what these online freelance companies are already doing. Is your non-profit's goal essentially to be marketers for these companies, letting people in less advantaged countries know that these opportunities exist?

The next question would be - how well are these companies ALREADY attracting poverty stricken people. Every person I've hired from upwork, when I asked them how they got into it, specifically mentioned trying to alleviate their own poverty. From that perspective, your non-profit could be creating the illusion of progress - helping raise the people you work with in belize out of poverty, while simultaneously taking jobs from other, poverty stricken people in EG india.

I think it would be helpful to ask more people in Belize what they think. Too often things are driven by what donors think, not by what would be good for the people a project is ostensibly trying to help.

Also, perhaps run a small-scale pilot project, then learn from that.

Has this been tried before elsewhere? If not, why not? If yes, what were the results?

I agree with ChristianKl. you said:

it is not expected to attract for-profit support, especially because it would probably not be a particularly profitable venture.

why won't it be profitable? Can't you make it profitable? There is a market failure connecting people in places where minimum wage is too high to employ locals with employees willing to work for less. (in that its not easy to hire an international team)

I would be interested in getting involved in a for-profit version of this idea. (and was taking small steps towards researching similar ideas)

Why do you want to do this as a nonprofit instead of a for profit company?

HPMOR is an excellent choice.

What's your audience like? A book club (presumed interest in books, but not significantly higher maturity or interest in rationality than baseline), a group of potential LW readers, some average teenagers?

The Martian (Andy Weir) would be a good choice for a book-club-level group- very entertaining to read and promotes useful values. Definitely not of the "awareness raising" genre, though.

If you think a greater than average amount of them would be interested in rationality, I'd consider spending some time on Ted Chiang's work- only short stories at the moment, but very well received, great to read, and brings up some very good points that I'd bet most of your audience hasn't considered.

Edit: Oh, also think about Speaker for the Dead.

Not sure what you mean by "positive" here. Ethically, what you probably want are works that make you take the perspectives of people different from you, and involve solving problems in creative and effective ways. Maybe I'll try making a list of those later, but right now I'm just going to focus on fiction that might inspire people's problem-solving skills a little.

Top Recommendations:

Online original fiction: Everything written by Ted Chiang (excepting "Understand," perhaps - that is not a story about ethical behavior :P). "The Man Who Bridged The Mist" by Kij Johnson. Possibly some selected Greg Egan stories, possibly Yudkowsky's The Sword of Good.

Book-form fiction: Tons of options here. Rosemary Kirstein's "The Steerswoman's Road" is quite good. Asimov's novel "The Gods Themselves" is a classic (if PG-13), can also direct them to an Asimov anthology like "I, Robot." More classics like Lloyd Alexander's The Iron Ring (one of those kids books that's still good for adults), lots of Ursula LeGuin (particularly her early stuff). Terry Pratchett (probably best to get people started with a later novel like Thief of Time, Small Gods, Wee Free Men, or Making Money).

Fanfiction: Luminosity, HPMOR, most things alexanderwales has written (all good, maybe not all what you want), and the superman fanfic Veritas are all pretty recommendable to general audiences. Another contender would be author Forthwith's My Little Pony short stories (not that their longer stuff isn't also good, it's just not finished).

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.