Preheat oven to 350˚F.
Place bread in a food processor and process into large crumbs or cut into ½-inch dice; you should have 12 cups. Spread bread over 2 large shallow baking pans and bake in upper and lower thirds of oven, stirring occasionally and switching position of pans halfway through baking, until completely dry, about 25 minutes. Transfer bread to a large bowl.
Increase oven temperature to 450˚F and grease a 13-by-9-inch baking dish with olive oil.
Heat olive oil in a large skillet over medium heat. Add sausage and cook, breaking up meat into small bits, until browned and cooked through. Remove with a slotted spoon.
To the same pan, melt 1 tablespoon butter and add celery, fennel, onion and apple, and cook, stirring occasionally until onions are tender and translucent, 8 to 10 minutes. Add white wine and deglaze pan by scraping the bottom with a wooden utensil and cook until wine has evaporated. Stir in thyme, sage, salt and pepper.
Add vegetable mixture and reserved sausage to bread crumbs and/or cubes, tossing to combine. Pour chicken broth over the bread mixture, tossing to coat evenly.
Spread stuffing in the prepared baking dish, dot with remaining butter and cover tightly with foil. Bake in upper third of oven until heated through, about 20 minutes. Remove foil and bake stuffing until top is browned, 10 to 15 minutes more.
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