For the bread pudding: Preheat the oven to 350 degrees F. Grease 8 medium ramekins with butter or cooking spray. Whisk together the eggs, milk, sugar, and 2 tbsp. vanilla extract. Mix in the mashed banana. Fold in the banana pieces, pineapple, coconut, and pecans.
Mix in the bread pieces and let sit for 1-2 minutes; stir gently to combine. Pour bread pudding mixture into greased ramekins and bake on a tray for 45-60 minutes or until cooked through and golden-brown on top.
Prepare cream cheese frosting: Beat cream cheese and butter with an electric mixer on medium-low speed until smooth. Gradually add in powdered sugar, beating at low speed until blended. Stir in remaining vanilla (½ tsp.) Increase speed to medium-high, and beat until fluffy, about 1 minute. Transfer to a piping bag when ready to serve. Optional: you can add milk, gradually, as desired, for a thinner consistency.
When bread puddings are finished baking, remove from oven and allow to cool slightly. Pipe frosting onto cupcakes in a lattice pattern; garnish with candied pineapple pieces. Serve.