Thanks for putting this out there. I found some weird things as well when using it, but just figured it was me. I was hoping your notes were from 2014, but it looks like you just went through all this.
Another problem with Pharo is the confusion with Bloc, Morphic, and Spec. With C# you have WinForms and that is pretty simple and Java has Swing. With Pharo, I can't seem to find a decent way to build a GUI. Is Spec supposed to replace Morphic?