In a large Dutch oven heat 1 tablespoon of the oil over medium-high heat. Add the sausage; cook for 5 to 6 minutes until browned, stirring occasionally. Remove sausage with a slotted spoon.
In the same pan cook onions and garlic for 2 to 3 minutes, stirring occasionally, until nearly tender. Add the squash; cook for 5 minutes. Stir in the chili powder, salt, and cayenne pepper; cook for 1 minute. Return the sausage to pan. Add broth; bring to boiling, then reduce heat. Simmer, covered, for 8 minutes.
Meanwhile, in a large skillet heat remaining oil over medium-high heat. Cook apple slices in hot oil for 4 to 5 minutes, stirring occasionally, until light brown. Transfer apples along with beans to chili. Simmer for 3 to 4 minutes until apples are tender. Top servings of chili with sage and apple rings.