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Heat olive oil in a large non-stick saucepan over medium-high heat. Crumble sausage into 1-inch pieces and add to saucepan.
Cook sausage, stirring occasionally until cooked through. Drain sausage onto a plate or baking dish lined with paper towels, set sausage aside.
Add diced bacon to saucepan, return to heat and saute 3 minutes, stirring occasionally. Add diced onions and saute mixture until bacon is cooked through and onions are translucent, about 3 - 5 minutes longer.
Add chicken broth, water, sliced potatoes, sugar, fennel seeds, and salt and pepper to taste. Bring soup just to a boil then reduce heat to medium-low and stir in cooked sausage.
Cover saucepan and simmer, stirring occasionally, until potatoes are nearly tender, about 10 - 15 minutes.
Add in kale then simmer until potatoes are soft and kale is tender, about 5 - 10 minutes longer.
Stir in half and half and warm through. Use a spoon or ladle to remove excess fat from top of soup if desired. Serve warm topped with Romano cheese.