On the latter parts, I'm currently an (early-career) college prof and would seriously consider switching to that model if it existed/worked. I'd much prefer tutoring people outside the institutional framework of curricula/grades/exams/lectures if it were reasonably stable work you could earn a living at, with genuinely interested students. There are some good things about the formalized education system, but in large part it's a compromise due to the need to produce some kind of credential employers recognize (related but not identical to "actual learning"), and to make budgets work.

Though I'm less interested if, like some tutoring jobs, it's just helping people cram for SATs, and especially if that's really seasonal work that only happens around SAT-time. So I wish you luck. :)