Hi all, I was quite interested to discover this thread and after trying out the new POC, thought time to bump the discussion.
In brief, I agree that adding actual shapes to tools that will (soon/future) be used for path operations and simulation will be another great step forward.
The POC dialogs & discussion on how it works, seems all headed in a good direction.
What I really struggled with was the SEVEN menu options and which one does what. Maybe it is is just draft menu text that can be improved?
My suggestion is keep existing one menu item, and instead just add two button ("Create Tool Controller(s)" & "Create Tool bit shape(s)") to the proposed tool Library dialog and maybe some moving buttons around and refining names.
A rather rough draft is attached below. Idea is that top right 4 buttons are library management, then center right are 3 tool management, with one tool bit shape button below that (currently abbreviated just to "New Shape" and the "Create Tool Controller(s)" on bottom left. The OK button, probably needs removing, and Cancel, probably should be located under the library buttons. If shape button text is long, it could also go at bottom.
I am not set on names or placement, just getting some ideas flowing.
....image is at bottom of post
Second, lessor thing I found a bit odd, was ability to create a new tool, without adding it to a library, but instead adding it to FreeCAD document root, so later you can create toolcontroller(s) from it. Why not instead just add to a/default library, then create use the standard way/button to create toolcontroller, instead of introducing a second way, which seems a bit unusual (dropping a path object in doc root!).