Beat chilled heavy cream until soft peaks form. Add 2.5 tablespoons powdered sugar and beat until stiff peaks form. Set aside.
In a large bowl, cream together softened butter, cream cheese, vanilla, and powdered sugar. Add prepared whipped cream and mix to combine.
Gently fold in blueberries, strawberries, peaches, and kiwis into the cheesecake filling. If raspberries are too soft, set them aside to scatter later when spreading the filling over the tortillas.
Stir vanilla instant pudding powder into the cheesecake mixture using a rubber spatula.
Refrigerate the cheesecake-filling mixture for about 30 minutes.
Spread the cheesecake mixture evenly over the tortillas, scatter raspberries on top, and roll tightly.
Brush each rolled tortilla with melted butter and roll in a cinnamon sugar mixture. Slice into 2/3-¾ inch thick portions.
Serve the rolls immediately.