Dan,
I am glad to see you and so many others excited about the possibilities that the Strongtalk release brings. The ideas you propose are very good too. So I hate to be the "been there, done that" pessimist and hope that what I write below will just encourage reflection but not cause anybody to give up.
In my experience projects tend to have personalities just as people do and tend to attract some kinds of people more than others. So while there is no technical reason why somebody couldn't write eToys in Python I will be very surprised if it happens, just like I don't really expect to see Squeak become a great Unix scripting environment or embrace native GUI widgets. These things are all possible but they would depend on having people working on such projects who are naturally attracted to different kinds of projects.
Of course you can pay somebody to work on something that they might not seek out on their own, or if you are their thesis advisor you can also get them to do it. My impression is that Craig Chambers and Urs Hölzle were more C++ guys than Smalltalk ones even though they did such fabulous work on the Self VM. This is based on things they said while doing the work, the feeling I get while reading their code and also the direction their carreers went after that project.
The source for the Self VM has been available since 1992. Perhaps the timing was wrong (people used to complain about having to upgrade their Sparcstations from 8MB to 24MB of RAM to run Self) and perhaps now different people are looking into this and will make it work. But my guess is that most people who enjoy Squeak will find the Strongtalk sources tiring and will end up moving on to other projects. I will note that Klein, the Self-in-Self, has also been open sourced and though I haven't looked at it yet I expect it will be far friendlier to Smalltalkers. Even Ian seems to have grown tired of the C world otherwise he would have been my best bet for making something interesting with Strongtalk.
For those Squeakers who do feel they can deal with the pain of a huge C++ system given the rewards that await them I can just say "you have my admiration and my thanks!"
-- Jecel