Roast the butternut squash
Slice off the top and bottom, slice it in half lengthwise, scoop out the seeds, and coat with olive oil, salt, and pepper. Place the squash flesh-side down and roast at 375 for 45 minutes, until a fork can pierce it with little resistance. Scoop out the flesh and measure 1 ½ cups.
Season the ground beef with the salt, Italian seasoning, sage, fennel, black pepper, maple syrup, red wine vinegar, and garlic. Brown over medium high heat, then remove from the pot and set aside.
Add the butter and olive oil to the same pot. Sauté the onion until softened, then add the garlic, oregano, and red pepper flakes. Stir in the tomatoes, roasted butternut squash, and chicken stock. Simmer for about 30 minutes.
Meanwhile, cook the rotini in generously salted water until al dente. Reserve at least ½ cup pasta water before draining. Return the pasta to the same pot after draining; we will mix some of the sauce into it later.
Blend the tomato and butternut squash sauce until smooth. Blend in the heavy cream and vodka, if using. Return the beef to the sauce and simmer for 10 minutes.
To the rotini pot, add enough sauce to coat it generously. Reserve any extra sauce for another meal. Add the Parmesan cheese and stir until melted into the sauce. If the sauce is too thick, add reserved pasta water a little at a time until it reaches a silky, creamy consistency. Taste and adjust the seasoning as needed.