Ok. So the Squeak objective for you might be something like: "Evolve mildly the current Squeak functionality. Fix bugs. Keep APIs compatibility.".
no, I'm not that conservative. better "evolve the current Squeak functionality, discuss possible show-stoppers publicly before implementing them so that existing projects can surf across major changes"
Squeak is dynamic enough for this to be possible, and not even difficult IMO.
Stef