To prepare the filling: In a mixing bowl, using an electric mixer, whip together cream cheese, powdered sugar, orange zest and vanilla until fully combined. Gently fold in sliced bananas by hand.
Divide creamed mixture between four tortillas. Top with a second tortilla. Place flat onto a sheet pan or platter. Cover with plastic wrap and refrigerate for 30 minutes. [It's important to chill the filling before cooking.]
To prepare: In a small bowl, mix together softened butter, brown sugar and cinnamon until fully combined.
Spread one side with cinnamon butter mixture then place buttered side down into a non stick pan. Brown over medium-high heat. While the first side is browning, spread the butter mixture onto the other side.
Cook on medium to medium-high heat until the quesadilla is golden then turn, repeating on the other side.. [The brown sugar caramelizes quickly, don't walk away from the pan]
Meanwhile, Heat caramel topping in a microwave safe bowl until it is the consistency of syrup. Mix in the rum.
To serve, cut quesadillas into quarters. Drizzle generously with caramel-rum sauce.
Garnish with powdered sugar and whipped cream or ice cream. Serve immediately.