This is a great idea but would need a lot of monitoring. There are a lot of dangers on the internet and not all the discord channels are child-friendly. So there would need to be a lot of monitoring or a way to keep them from other chat rooms. Plus you state:

"The plan is to get these students, who for the most part are digital natives and already using these tools, to earn money for the activities they already do online. "

You state the students are 9-18. The legal tax issues of this are complicated depending on where you live. In most of the states of the United States, if the child is under a certain age the money has to be put into a trust until they reach a certain age. The money could not be used to further the education platform. I love the idea and these are a few points that would need to be clarified.

I am a previous homeschooler and would love to do it again. However, my state is not a supporter of homeschooling so there is no funding for it. Seeing as we do not have the $7000 to go to an online public school to meet the requirements without searching out our own program, we are opting for traditional schooling. This would be great to help parents who do not wish to use the public school system or have no options.