In a large bowl, combine the pumpkin, brown sugar, 1/2 and 1/2, and pumpkin pie spice. Set aside.
Spoon 3-4 tablespoons of the pumpkin pie mixture into the middle of each tortilla. Fold in the sides and then roll up the tortilla, creating the chimichanga shape. Lay on a non-stick baking sheet (or sprayed baking sheet) seam side down.
In a medium sized bowl, mix together the oil, butter, sugar, and cinnamon. Using a pastry brush, liberally brush the top of each chimichanga with the butter/oil mixture. (the more the better!)
Cook the chimichangas for 8 minutes. Remove from oven and flip, brushing the underside with more butter/oil mixture. Place back in the oven and cook for an additional 6 minutes.
While chimis are cooking, prepare the icing. Mix together the powdered sugar, skim milk, and vanilla. Stir until fully combined. Add more sugar if you want the icing to be thicker.
Remove the chimis from the oven and flip to have the seam side down again. Allow to cool for about 5-10 minutes before spooning on the icing and serving. You can also top with cool whip or whipped cream! Enjoy!