Coat a large dutch oven with the 1-2 Tbsp olive oil. Add the sausage, crumbling and breaking up with a big spoon until fully cooked, and remove to a plate. Add the chopped onion, celery, carrots, and squash, sautéing until softened and lightly browned on the edges, about 7-8 minutes. Tie the thyme and rosemary into a bundle, and add it to the pot with the garlic and potatoes, stirring to combine with the other vegetables. Season with 1 tsp each of kosher salt and cracked black pepper.
Add the 1/2 cup wine to the pot to deglaze, and then the crushed tomatoes (with their juices), bay leaf and the chicken stock. Last, throw in the parmesan rind! Bring to a simmer uncovered for 25 -30 minutes, stirring occasionally.
When the vegetables are all fully cooked, add the beans, the cooked sausage, the chopped chard or spinach, the pesto, and the grated parmesan. Stir to combine, and finally add the parsley. Season to tase with additional salt and pepper as needed. Discard the bay leaf and herb sprigs.
To serve, preheat the broiler. Slice the baguette into 12 1 inch slices, and arrange in a single layer on a baking sheet. Coat each slice with olive oil, parmesan cheese, kosher salt and pepper, and broil until the cheese is bubbly and golden brown, about 3 minutes. Ladle the soup into bowls and float a couple of the baguette slices on top. Finish with extra parmesan and parsley.