Everything I write below about pedagogy is anecdotal, and I don't have much experience outside of being a student.
As a former teacher I complete agree with your approach. One critical component of teaching is determining your students' next inferential step. Which is easier in a "one to one" setting, and almost impossible in a "one to many" setting.
Various online lessons are an exercise in frustration because always someone complains they are too easy (that they cover only the "obvious" and "well-known" facts), and someone else complains they are too difficult (that they use terms they didn't explain, and go through complex ideas too fast).
Traditional school solves this by making everyone progress along the same path, and the same speed. I guess we all know how frustrating this is for smart people who have a potential to do much faster. On the other hand, LW audience will consist of smart people, but there will be wild differences in background knowledge.
So the approach "this is the outline, read these things in this order, and discuss with me when you complete something or you get stuck" is a good solution that allows you to provide material for many people at the same time, and yet address everyone individually.
Some online courses have separate Q&A threads for each lesson, where students can talk to each other, but only about the specific lesson.
Update 7/9/17: I propose that Learners individually reach out to Teachers, and set up meetings. It seems like the most practical way of getting started, but I am not sure and am definitely open to other ideas. Other notes:
Update 6/28/17: With 14 people currently interested, it does seem that there's enough to get started. However, I'd like to give it a bit more time and see how much overall interest we get.
Idea: we coordinate to teach each other things via video chat.
So, this seems like something that would be mutually beneficial. To get started, we'd need:
Personally, I'm not sure how much I can offer as far as doing the teaching. I worked as a web developer for 1.5 years and have been teaching myself computer science. I could be helpful to those unfamiliar with those fields, but probably not too much help for those already in the field and looking to grow. But I'm interested in learning about lots of things!
Perhaps a good place to start would be to record in some spreadsheet, a) people who want to teach, b) what topics, and c) who is interested in being a Learner. Getting more specific about who wants to learn what may be overkill, as we all seem to have roughly similar interests. Or maybe it isn't.
If you're interested in being a Learner or a Teacher, please add yourself to this spreadsheet.