Complex sentence: Walter tended to be rather old-fashioned, despite his being progressive, even going as far as to stoop to emotional blackmail to get Maude to be a more traditional housewife.
Split into simpler sentences: Walter tended to be rather old-fashioned, despite his attempts at being progressive. Sometimes, he would even go as far as to stoop to emotional blackmail to get Maude to be a more traditional housewife.