Working mode off.
Chatting mode on.

In short, the main issue is lack of modularity.
As you may know this is one of the primary concerns of current board &
release team.
We have to deal with this, and deal nicely. Otherwise squeak will be
buried under cruft of 'irreducible complexity'.

Smalltalk, by its nature does not defines a high-level abstractions
which can be called 'module' or 'package'.
In many other languages this concept included as basic one, while in
Squeak we stick with an image-based concept,
where image is a big monster with untamed complexity, where changing
any piece of code could lead into breakage in unpredictable place(s),
because everything is late bound.

I'm aware of at least two of module-based solutions for Squeak:
- Spoon by Craig Latta
- Namespaces by Michael van Der Gulik , as part of his SecureSqueak project

Both systems currently in development. And almost 99% it is solo
development by their authors.
Both systems having own pros and cons , and it's hard to decide (as
for me), which is better for the future of Squeak.

Why we don't see these systems already employed?
Currently we have so-called 'status-quo'.

I think , the main problem is more social than lack of manpower or
funding: There is no high pressure from squeak community (and nobody
having an ultimate power to force it) to abandon obsolete concepts,
sacrifice ST-80 compatibility (partly) and move forward with system
based on better design & modularity.

Chatting mode off.
Working mode on.

-- 
Best regards,
Igor Stasenko AKA sig.