Preheat oven to 325 degrees F (165 degrees C). Line 24 cupcake cups with paper liners.
In a mixing bowl, stir together the Amish friendship bread starter, eggs, vegetable oil, 1/2 cup milk, sugar, 1/2 teaspoon of vanilla extract, baking powder, baking soda, and salt until thoroughly combined. Mix in the flour and cherry gelatin powder. Spoon the batter into the prepared cupcake cups.
Bake until a toothpick inserted into the center of a cupcake comes out clean, 20 to 25 minutes. Let cool.
In a large bowl, beat the vegetable shortening with butter with an electric mixer on medium speed until fluffy, and add the vanilla extract. Beat in confectioners' sugar, 1 cup at a time, stopping often to scrape down the sides of the bowl; mix in the milk, and beat until the frosting is light and fluffy. Spread on cooled cupcakes. Sprinkle each cupcake with a few white chocolate chips, if desired.