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This might be a patch for the problem, but it works.
I noticed that Blender doesn't update the UI after creating a new workplane.
Before
I noticed that it creates the new workplanes, but doesn't update the changes.
After
This is when I force the update after the workplane creation
Windows
Blender 4.0
CAD_Sketcher: latest
(I don't want the bounty. Too much for such a small change)
Edit: Hmm, I just thought about it. It might cause some performance problems for bigger projects. But at least I found the problem.
With that said, I'm not sure if it's avoidable to not re-draw.