Heat a large pot on high. Sprinkle salt on top of beef. When pan is hot, add in beef and Italian sausage and brown for meat 5 minutes, breaking apart into small pieces. Use a spatula to smash any clumps of meat and break them apart.
Then add celery, carrot, onion, and garlic. Sauté 5 minutes
Then add tomato paste, butternut squash, crushed tomatoes, salt, pepper, sugar, and crushed red pepper flake.
Add in red wine and simmer on medium low heat for 30 minutes.
Then add milk and simmer on medium low heat for 30 minutes.
Add in roasted squash into the sauce. Taste for seasoning. Add salt, pepper, or sugar as needed. The sauce should taste savory and slightly sweet.