Preheat oven to 350 degrees. Toss cubed bread with 3 tablespoons olive oil, salt, and pepper. Spread on a baking sheet and bake until bread is crisp, about 30 minutes.
Heat vegetable oil in a large pot over medium-high heat. Crumble in sausage and cook, stirring until brown. Remove sausage; discard oil. Reheat pot over medium heat. Add 1/4 cup olive oil, and heat until hot. Add garlic, carrots, fennel, leeks, and onion, and cook, stirring occasionally, until softened. Add wine and raisins. Season with salt and pepper. Simmer about 3 minutes. Stir in sausage and red pepper flakes. Remove from heat. Stir in nuts, herbs, bread, stock, butter, and eggs. Mix well.
Mound 1 1/4 cup stuffing mixture into 1/2-cup capasity buttered muffin tins. Bake until golden and crusty on top, about 30 to 40 minutes.