Place bell peppers into oven and cook until skin is papery and blackened, about 35-45 minutes. Remove and transfer peppers to a bowl. Cover with plastic wrap and let the peppers steam in the bowl.
On a large baking sheet combine the zucchini, squash, onion, garlic, basil, fennel, oregano, red pepper flakes, olive oil, kosher salt and black pepper. Toss the vegetables until well coated with the oil, herbs and spices. Add the sausage and spread everything into an even layer on the baking sheet. Roast for 35-40 minutes. (Note the vegetable/sausage mixture can roast in the oven at the same time the peppers are cooking)
While vegetables are roasting, prepare the pasta and cook until al dente. Rinse with cool water to stop the cooking process and drain. Set aside.
When the peppers are cool enough to handle, remove the skins, stems and seeds and cut the peppers into thin strips. Transfer peppers to a large bowl. Add the roasted vegetables and sausage to the peppers. Scrape the pan to get all of the juicy goodness into the bowl. Add the olives, capers and red wine vinegar. Toss to combine.
Transfer the pasta to a large serving bowl. Top with the vegetables and all the juices. Sprinkle with fresh basil and parsley. Serve.