The Squeak community agrees that Squeak badly needs improved documentation. Squeak is fast changing, so hardcopy documents will likely grow obsolete fairly fast.
This is a very important, and neglected, area of Squeak development. It may be the most vital thing to PromoteSqueak
Most proposed solutions involve documenting Squeak within Squeak, using what are, basically, program comments on steroids.
Some such systems have been invented and analysed for other languages, by other people.
A seminal thinker in this area is Donald E. Knuth, Professor Emeritus of The Art of Computer Programming at Stanford University. He promotes a discipline called Literate Programming (see an overview there). Literate Squeaking is Squeak specific Literate Programming.
Efforts:
Dan Ingalls implemented HypertextClassComments. Hypertext links withing class comments are possible now, but they are rarely used.
See PaulFernhout's page on Monticello Basics, and let your imagination run wild. Think of the possibilities for teaching programming, Smalltalks and Squeak!
