anything is doable. The barrier always is knowledge.��
There is already a project to bring documentation and a specific kind of documentation called Pillar which is what we use for updated PBE and Pharo for the Enterprise books inside the GTInspector. Its a WIP.
On the side of GTSpotter you have a morphic wrapper called Brick that is used to ease the design of the GUI.��
But whether you use Glamour or Spec or Brick or whatever you use Morphic. Only Bloc which suppose to be the new kid in the block to replace Morphic is not Morphic but for now at least the heavy weight gorilla is Morphic. As soon as you understand morphic you are unstopable.��
Dynamic documentation is one of the things that Pharo really lacks if you ask me, I am that annoying guy that complains about documentation all the time. I think however that we get closer to this .��
From what I see you talk about class and instance comments. Of course with Pillar at your side you can go way above that and provide functionality that can rival pdf and html help files.��
So yes its doable and yes you can take it very far but as always is about having the will to do the hard work because in the end nothing is easy as it looks or else someone else would have done it by now.��