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Putting print statements in that part of the world shows that the reason why the list.remove fails is that while a ColorDelegator.toggle_colorize_event object is in the list, it has a different memory address than the ColorDelegator.toggle_colorize_event object to be removed. I've seen this NOT fail occasionally (the memory addresses were the same, so the list.remove succeeded), all of which would seem to imply that something has moved in memory.
I'll mention that when the failure occurs, the list always has just one object, a ColorDelegator.toggle_colorize_event object.