The post talks more about usability issues rather than any theoretical issues. There are more fundamental objections to typed holes - but Wingman is kind of th

The post talks more about usability issues rather than any theoretical issues. There are more fundamental objections to typed holes - but Wingman is kind of the answer to those concerns - with typed holes you're filling in types from the expressions, with Wingman you're doing pretty much the opposite - synthesizing programs from the type. Now there might be usability issues with Wingman as well, but it represents a different direction - more suitable for type-driven development.