Preheat oven to 325 degrees F. Grease and flour a 9" x 5" loaf pan. Set aside.
In a medium bowl, whisk together flour, baking powder, baking soda, salt, and cinnamon. Set aside.
In a stand mixer fitted with a paddle attachment, blend the oil and sugars until combined.
Add the eggs one at a time, scraping down the bowl between each addition.
Add the bananas, buttermilk and vanilla and mix to incorporate.
Remove from the stand mixer and using a spatula slowly stir in the dry ingredients just until barely incorporated.
Gently stir in the chocolate chips being careful to not overmix.
Pour into prepared loaf pan and drizzle caramel sauce over top avoiding the edges near the pan. Only use about 1/3 of the mixture you made.
Bake for 60-70 minutes until a toothpick inserted comes out clean. The loaf will be a rich brown color. Let rest for 20 minutes in the pan then carefully turn the loaf out and onto a cooling rack.
Drizzle half of remaining caramel onto the loaf while it is warm.
Bring heavy cream to simmer over medium heat in a small sauce pot. Leave on stove top to use shortly.
Add sugar, cream of tartar and water to a 3-4 quart, heavy bottomed sauce pot over medium high heat. Stir together once being sure to not splash the sugar onto the sides of the pot.
Allow to come to boil. Wash down the sides of the sauce pot twice with a wet pastry brush to flush any sugar crystals down into the cooking sugar.
As the sugar cooks it will begin to turn amber colored. If it's becoming amber unevenly or in just one spot, gently swirl the pan (do not stir) to even out the color. Once the pot is a deep, rich amber remove from the heat.
Add the heavy cream and stir with a whisk vigorously. The sugar and cream will foam, and increase in volume and release a lot of steam. Be cautious to not burn your hands. Add butter pieces and vanilla once the cream is fully whisked in.
Pour into a heat proof container and allow to cool completely before using.
I like to make my own buttermilk since I don't use enough to purchase a quart at a time.
To make a 1/4 cup as called for in this recipe, I add 1/2 tsp white vinegar to a 1/4 cup measuring cup. Then I fill the rest of the cup with lowfat milk. Let it sit for 5 minutes before adding to your recipe.
To make a full cup of buttermilk this way, start by adding 1 Tbsp of vinegar to a 1 cup measure and fill the rest with lowfat milk.
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