Preheat oven to 350°F. Grease a 9x9-inch baking dish (or an 11x7-inch dish).
In a large skillet, melt 2 Tbsp butter. Add apples, brown sugar, flour, cinnamon, nutmeg, and salt. Cook for 5–7 minutes, stirring occasionally, until apples begin to soften and caramelize. Stir in vanilla and maple syrup. Transfer to the prepared baking dish.
Make the maple caramel sauce: In a small saucepan, combine brown sugar, butter, heavy cream, and maple syrup. Simmer over medium heat for 3 minutes, stirring until slightly thickened. Remove from heat and stir in a pinch of sea salt.
Combine and layer: Pour all of the maple caramel sauce evenly over the apples in the baking dish.
Prepare the cobbler topping: In a bowl, whisk together flour, sugars, baking powder, cinnamon, and salt. Cut in cold butter with a pastry cutter or fork until crumbly. Stir in milk just until combined (batter will be thick).
Assemble: Drop spoonfuls of topping evenly over the caramel-coated apples, leaving small gaps for bubbling.
Bake: Bake for 35–40 minutes, until the top is golden and the filling is bubbling around the edges.
Cool slightly before serving. Serve warm with ice cream or whipped cream.