1. Heat olive oil in large pot over medium-high heat; add sausage and cook, stirring until caramelized, about 5-6 minutes. Remove with slotted spoon; set aside.
2. Add onion and cook, stirring, until softened, about 3-4 minutes.
3. Add garlic, thyme, and vinegar. Cook, scraping bottom of pan, for about one more minute.
4. Add chicken broth, squash, salt and pepper; bring to a boil. Reduce to medium-low heat and simmer, covered, until squash is tender, about 30 minutes.
5. Transfer to blender; blend until smooth.
6. Return to pot. Thin with water, if needed. Serve topped with sausage, more freshly cracked black pepper and a drizzle of olive oil.

Garnish options Crispy Fried Parsnip Chips: Use a vegetable peeler to slice long thin strips of parsnip. Lightly fry in canola oil until slightly darkened and crisp. Drain on paper towel. Gently place wide ends into soup so chips stick out. Mixed Herb Sour Cream: Mix high-fat sour cream with a mix of finely chopped dill, parsley and basil and let sit for at least 30 minutes. Serve each bowl with a generous dollop on top.