After much deliberation and inspection, much simpler fix

Author: weswigham

src/compiler/checker.ts

@@ -13535,7 +13535,7 @@ namespace ts {
         // be "pushed" onto a node using the contextualType property.
         function getApparentTypeOfContextualType(node: Expression, checkMode?: CheckMode): Type {
             const type = getContextualType(node, checkMode);
-            return type && getApparentType(type);
+            return type && mapType(type, getApparentType);
         }
 
         /**

tests/baselines/reference/contextualTypingOfOptionalMembers.types

@@ -90,8 +90,8 @@ declare function foo<T extends Bar>(x: string | T): T;
 >T : T
 
 const y = foo({
->y : Bar
->foo({    bar(x) { // Should be typed number => void    }}) : Bar
+>y : { bar(x: number): void; }
+>foo({    bar(x) { // Should be typed number => void    }}) : { bar(x: number): void; }
 >foo : <T extends Bar>(x: string | T) => T
 >{    bar(x) { // Should be typed number => void    }} : { bar(x: number): void; }