Smalltalk simply has poor workflow from the programmers perspective, compared to what he's used to.
It may be awesome. But no one will ever know, because it's too different from the normal developer's work flow to easily gain adoption, even if the benefits are substantial.
Could something like Smalltalk work in such a way that the "image" is a series of files and folders, so if something goes nuts we can do what we always do and poke around in the data?
Could automatic code reloading and online introspection be applied through a more traditional client (debugger) - server (running process) setup?
Something like that may have a better chance. This machine ain't got time to slow down and make repairs.