In a mixing bowl, mix together the softened cream cheese, powdered sugar, orange zest and vanilla. Mix until fully combined, then gently fold in the sliced bananas.
Divide the mixture between the tortillas. Onto one half of each flour tortilla spread the cream cheese filling. Fold the tortilla over the cream cheese filling.
Repeat this with all four tortillas and place flat on a platter. Cover in plastic wrap and refrigerate for 30 minutes. [It's important to chill the filling before browning.]
In a separate bowl, mix together one stick of softened butter, 1/4 cup of light brown sugar and 1 tsp of ground cinnamon.
To prepare the quesadillas: Spread one side with the cinnamon butter mixture then place 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-high heat until the quesadilla is browned then turn, until golden on both sides. [The brown sugar caramelizes quickly, don't walk away from the pan]
Heat the caramel topping in a microwave safe bowl until it is the consistency of syrup.
Add the rum flavoring then drizzle over the hot quesadillas before serving.
To serve, cut the quesadilla in half and drizzle generously with the caramel-rum sauce.
Garnish with powdered sugar and whipped cream.