In a bowl and using a hand mixer, beat the heavy cream until it begins to thicken. Add the powdered sugar and continue to beat until stiff peaks form. Set the whipped cream aside.
In another bowl, mix cream cheese, pumpkin, sugar, vanilla and pumpkin pie spice together until well-blended. Gently fold in the whipped cream until the mixture is well-combined.
Refrigerate about 1 hour, or until cheesecake is firm. Mix 1/2 cup sugar and 1 tablespoon cinnamon in a plate. Set aside.
Place about 1/4 cup cheesecake on the lower 1/3 of a tortilla, and roll each tortilla up and put on serving plates.
In a large skillet melt butter over medium to medium-high heat. Place tortillas seam side down and fry just until crispy and golden, 1-2 minutes per side.
Roll the tortillas in the cinnamon-sugar mixture until fully coated. Top with caramel sauce and serve.