>I've come to the conclusion that C is best understood if you think about it in terms of the way that an assembly language programmer would think about doing things
I agree with this. I found another article that made the transition for someone coming from something like Python or Ruby easier. It shows how to use gdb as a sort of C REPL. https://www.recurse.com/blog/5-learning-c-with-gdb
The quick feedback loop certainly makes things like pointers, arrays, etc, more clear.