Squeak 3.3 was an effort to evolve into a modular system that would address most of your complaints, but it was abandoned and 3.4 was based on the monolithic 3.

Squeak 3.3 was an effort to evolve into a modular system that would address most of your complaints, but it was abandoned and 3.4 was based on the monolithic 3.2 instead. Smalltalk V/Win from the early 1990s, on the other hand, did a pretty good job. Your image was saved as v.exe which started out essentially empty while the actual VM and the system classes were stored in a bunch of immutable .dll files. As you developed in the same style as in any other Smalltalk, the v.exe file would grow and grow with all the stuff that was particular to your application. You would then distribute that plus a subset of the .dll files (those needed to run you application but not to develop it).