As an example, when I was taught calculus of variations, we didn't dwell too much on the fact the symbols in our functions we were differentiating were no longer corresponding to points in R^n, but rather to functions existing in function space. Why the mathematics we were taught in Vector Calculus worked here as well was quietly ignored, to the extent that when I raised the issue with classmates, they didn't realize that anything had changed from vector calculus.
As another example, is physicists playing fast and loose with what exactly they mean by 'vector' (hint: they mean it's really a function on R^3, but good luck finding an undergrad textbook that says that; I'm curious as to how Sussman treats this).
Sussman, by virtue of implementing programs, takes a constructive approach, and thus forces both the author and reader to come to an explicit understanding of what the underlying mathematical objects actually are and the structure of how solutions are formed. Thus, I am not surprised that he comes up with a superior and clearer definition of the Legendre transform.