Hey thanks for the advice, you're spot on in every way. I've been at this for a while actually and have done all the things!
EdX is the best free online video based stuff I've found, plus the speaker acts likes he's on crack so it never gets boring lol
Code the Hidden Language of Computer Hardware and Software is a book that has been great for starting from absolutely nothing
Inside the Machine is a book that is awesome but not for starting from scratch, you gotta know some stuff first
Haven't messed with Python much, but have created various CLI's via Node, Ruby and Rust
Also a huge fan of shell scripting (Bash in my case)
Currently fiddling with the Rust language more and more, playing with libraries that interface with openGL to try and make some crappy 2D games
You're very right about assembly not being great on the pi, I fiddled with an Arduino 3+ years ago and was pleasantly surprised how easy it was to program (thought it would be harder going into it). I don't really have that anymore but I do have a pi lying around which is why I started seeing about fiddling with that for some basic assembly stuff. I'm probably gonna put that on hold now though and just wait for the X16 release, since it is literally everything I've been wanting.