Position racks in the upper and lower thirds of the oven and preheat to 400°. Wrap a piece of bacon around each persimmon wedge; secure with a toothpick and arrange on 2 parchment paper-lined rimmed baking sheets. Roast for 20 minutes. Flip the wedges, rotate the pans and increase the heat to 425°; roast until the bacon is crisp, about 20 minutes. Brush with the sherry vinegar and season with salt and pepper. Serve immediately.