There are several ideas floating around about ways to improve Squeak. Almost every suggestion has at least a little opposition from people who like it just they way it is. Here are some of the topics that have gone around.
Auto-Initialization – How many times do we type "super new initialize" before we factor it out?
Bistro is a new language that try to integrate Smalltalk and Java. There are a lot of features here that we can incorporate.
UML Modeling with live source code & diagram synchronization.
Take a look at Packages for connecting elements a UML diagram
Should be fairly easy to build a UMLClassDiagramMorph using(StringMorph, PluggableListMorph, PluggableListMorph) inside a RectangleMorph PastUpMorph. The StringMorph gets the class name, the first list gets instance variables, the second gets methods (May need to filter inherited items). The list items should be linked to open a method editor, providing easy access to the live source code. To build a simple inheritance diagram perhaps you start with a derived class, drop it into a PlayField, then select 'Model Ancestors' from a menu that will go from superclass to superclass emitting and linking class diagrams.
Introduce a keyword or other means to flag a method as abstract instead of having the convention of executing 'self subclassResponsibility', which violates the semantic coherence between an abstract method and its concrete implementations
Models of Computation References. There's a lot of good stuff out there, particularly for programming wide-area distributed systems. From E to Ptolemy to Lustre, here's a reference list.
DRINK ME is an exploration of macro-like capabilities.
New Modules is an exploration of, well, a new design for modules in Squeak.
Russell Allen - there have been a number of attempts to improve Smalltalk by eliminating classes. Probably the most famous became the Sun Improving Smalltalk project, whose windowing system became Squeak's Morphic.
UIIdeas - Squeak's user interface has untapped potential.