Whisk flour, white sugar, baking powder, cocoa powder, and salt together in a bowl.
Beat buttermilk, melted butter, eggs, 2 teaspoons vanilla extract, and vinegar together in a bowl until smooth. Stir red food coloring into buttermilk mixture. Mix buttermilk mixture into flour mixture until just combined.
Preheat a waffle iron according to manufacturer’s instructions.
Beat cream cheese and softened butter together in a bowl using an electric mixer until smooth and fluffy. Gradually mix 2 cups confectioners’ sugar into cream cheese mixture, alternating with milk and 1 teaspoon vanilla extract, until glaze is smooth.
Spoon 1/4 to 1/2 cup waffle batter into preheated waffle iron. Cook according to manufacturer’s directions. Repeat with remaining batter.
Lightly dust each waffle with remaining confectioners’ sugar, drizzle with glaze, and top each with whipped cream and strawberries.
You can substitute Splenda(R) for the sugar in the waffle batter.
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