For the past few weeks, I’ve been going back and forth with the notion of hiring a private tutor/teacher (not in school and not for work) that’s in a PhD program at a local uni for a few months. For the past +5 years, I’ve been teaching myself programming, math, and any related matters, yet it’s a slow and grueling process with many side paths that I go down. I’m tired of this! I want to dive into a book on financial…
Sounds like you need to take a graduate level course in derivatives modeling. Graduate level courses are typically seminar style and have lots of hands on work and discussions.
You might be able to find a school that does this kind of course online. I'm not sure how that would work for seminar style classes, but it might be what you're looking for.
Another option is to hire a tutor, as you said.
Just do it. See how it goes. Go on "Rate My Prof" or whatever and find someone who will challenge you (and who also cares that you learn). Have deliverables ("homework", readings, etc.). Be willing to pay them up front for developing your "class" syllabus. Planning how to teach complex materials is an arduous task, especially because most text-books aren't quite right for any given person's learning/teaching method.