Heat olive oil in a heavy-bottomed skillet over medium heat; stir in onion. Cook and stir until onion has softened and browned, about 5 minutes. Add bacon crumbles; cook for 1 minute. Stir in sweet vermouth, ancho chile powder, chipotle powder, and cinnamon. Reduce heat to low and stir in pumpkin; simmer for 5 minutes. Stir in half-and-half until smooth.