Make the caramel whipped cream: Combine sugar and water in a small saucepan and place over medium heat. Stir to melt the sugar until mixture starts to simmer. Stop stirring, and let the sugar caramelize. When sugar is a deep amber color, remove from heat and slowly add cream while stirring (it will hiss and bubble up). When all of the cream has been added, return to heat and stir until fully combined. Pour into a bowl and allow to cool and place in refrigerator to fully cool.
Make the caramelized apple: Peel, cut in half, and core one apple. Stir 2T of sugar and a couple teaspoons of water together in a small saucepan and place over medium heat. Let sugar caramelize without stirring, and add butter when sugar is amber colored. Once butter is melted, add the apple halves and stir to coat. Once the apple is slightly softened on the outside, remove from heat and set aside. When cool, chop into pieces, to be folded into cupcake batter.
Make the cupcakes: Preheat oven to 350 degrees F. Place 12 cupcake liners in a muffin tin. Combine flour, salt and baking powder in a bowl and set aside. Cream together the butter, sugar, and brown sugar. Add egg one at a time and beat well after each addition. Stir in the vanilla, and slowly stir in milk. When combined, add the flour mixture and stir/fold to combine, making sure not to over-stir. Fold in the chopped apples. Spoon into cupcake liners and bake for 20-25 minutes or until toothpick comes out clean.
When cupcakes are completely cool, beat the caramel whipping cream until medium stiff. Pipe caramel whipped cream onto cupcakes and garnish with a piece of apple (if using fresh apple, make sure to treat with lemon or salt water so it doesn't brown).