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The remaining issue seems to be in this part. When I enable the delegate on both widgets, it fails.
self.journey_delegate = JourneyDelegate(self.tdt_model, self.day_type_model, self)
# Apply RightToLeft to the left table
self.table_widget.left_table.setLayoutDirection(Qt.RightToLeft)
self.table_widget.left_table.setItemDelegate(self.journey_delegate)
# self.table_widget.right_table.setItemDelegate(self.journey_delegate)
When I explicitly make a left delegate and right delegate error gone.