Stir strawberries and balsamic together in a large bowl. Cover and refrigerate until ready to use.
Preheat the oven to 400 F. In a large bowl or food processor, mix the flour, sugar, baking powder, baking soda and salt together until combined. Add the cubed cold butter and cut into the dry ingredients with a pastry cutter or pulse several times until coarse crumbs form.
If using a food processor, transfer the mixture to a large bowl. Pour 1 cup of buttermilk over top and fold everything together with a rubber spatula until it begins to come together. The dough will be shaggy and crumbly with some wet spots.
Pour the dough and any crumbles onto a floured work surface and using your floured hands bring the mixture together. Flatten the dough into a 3/4-inch thick rectangle. Turn horizontally and fold one side into the center and then the other side. Gently flatten into a 3/4-inch rectangle. Repeat the folding and flattening 2 more times ending with a 3/4-inch rectangle.
Cut 3" circles out of the dough. Rerolling and flattening any scraps to cut more circles. Arrange circles into a well seasoned 10" cast iron skillet or on parchment paper (or silicone baking mat) lining a baking sheet. Brush tops with buttermilk and sprinkle with coarse sugar.
Bake for 18-22 minutes or until the biscuits are golden on top. Remove from the oven and allow to cool before using. Beat the heavy cream until medium-stiff peaks form. Add vanilla and beat for 1 minute more. Serve: Slice the biscuits in half and layer with strawberries and whipped cream.
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