I think we have to improve the foreknowledge about what will happen, why it will happen, what it will mean, what are the related issues etc. I in most cases I have no clue about changes in package structure of the image that are being performed and that require changes in Pharo Kernel processing, initialization etc. As an example I can mention recent CodeImporter integration.
I like the improvements rate but as the side effect it makes Pharo less attractive platform for serious development.
Why? People should not develop in the bleeding edge of the system or at least they should know what they do. I use pharo bleeding edge daily and fix as soon as something goes wrong. Today we even improve Monticello browser feedback and version browsing. Stef