I would like something inspired by Cunningham & Beck's graphic debuggers/inspectors described in their
paper, available at http://c2.com/doc/case87.html  My own favorite method of learning a complex system
is to take an understandable-looking part of it, and crack open each subpart until I get to the
fundamental particles.  For example, I will look at C source code and highlight each function call,
then when I think I understand the overall picture, find the source for each function and do the same
thing.  What would help me do this in Smalltalk would be the ability to turn on hyperlinks in the
source for each message sent by the method, which would use a type-inferencing system to "drill down"
into the most likely mehtod source for the message.  If I am using a debugger or inspector, I would
like to follow links graphically (or via hyperlinks) between objects down to the SmallIntegers and all
the way back to Smalltalk.  It's certainly not for everybody, but hopefully some of the ideas here
will get you thinking.