The difference between Blender and Squeak if we look at them as
products that Blender is _end-user_ product, while Squeak is platform
without any end-user products.
While Blender requires a lot to learn for some of newcomers, it's
targeted on specific tasks: 3D design/rendering and postprocessing.
And Squeak by itself is nothing more than a base platform for
developing applications (like Blender).
A squeak VM/image plays same role as operating system for Blender: you
have to install some applications for working on specific tasks.

So, it's really different. Nobody willing to donate/fund operating
systems. People may want to fund specific projects, which developed to
deal with specific tasks in specific areas (web/3D design etc), but
not operating systems, which is too generic and basic and not targeted
to be used by end-users.


-- 
Best regards,
Igor Stasenko AKA sig.