To my knowledge, this has never, ever, worked well enough in a dynamic environment. Smalltalkers have spent over 3 decades trying to get this to work. What became the Smalltalk industry standard? Some form of code loading, often based on source code management.

Anyone who is doing tooling/library work in a dynamic environment needs to delve into the history of Smalltalk and ask if it was already tried and what the problems were. Chances are, it was already tried, and that there's useful experiential data there.