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In a large pot or Dutch oven, heat the oil over medium-high heat.
Pat the beef pieces dry with a paper towel and season them liberally with the salt and pepper. For 2 lbs of meat, I use roughly 3 teaspoons of kosher salt and 1 teaspoon of black pepper. It sounds like a lot, but the meat needs it and can take the seasoning!
Place the flour in a shallow bowl or on a plate and lightly dredge the beef pieces in the flour. You want them lightly coated.
In batches, add the beef to the hot pot and cook for 2 minutes per side, until a deep brown crust forms on all sides of the beef. This part can take 10-15 minutes. Don’t rush it. The caramelization of the meat early on gives the resulting sauce incredible flavor.
Remove the browned beef from the pot and set on a plate. Add the sausage to the pot and crumble with a wooden spoon or spatula, cooking until it is browned and crisp in spots.
Remove the sausage from the pot and place it on the same plate with the beef.
Reduce the heat to medium-low and add in the onion and a pinch of salt. Cook, stirring frequently, for a few minutes or until the onion begins to soften.
Add in the garlic, dried herbs, and red pepper flakes and cook for a few more minutes.
Add in the tomato paste and stir it around until it is melted and coating everything else in the pan.
Increase the heat to medium-high and allow the tomato paste to caramelize a bit on the bottom of the pot.
Add in the wine, scraping up the brown bits off the bottom of the pan as you pour it in. Keep scraping/stirring until all the brown bits have come off the bottom of the pot.
Bring the wine to a simmer and then add in the plum tomatoes, bay leaves, sugar, and balsamic vinegar. I like to break the tomatoes up some with my spoon/spatula. They release their juices right into the sauce.
Bring the mixture to a simmer and then add the beef and sausage back into the pot, along with any juices that may have accumulated on the plate. Add in some more salt and pepper (this is really a “to taste” kind of recipe – add as much or as little as you like).
Simmer the sauce over low heat for 3-4 hours, partially covered, or until the beef is very tender and falling apart. Shred some of the beef pieces into the sauce and leave some whole – this adds interesting texture.
Taste the sauce and adjust the seasoning as needed. Sometimes it needs a touch more salt, pepper, or even sugar. This will depend on the acidity of the canned tomatoes you use.
Stir in the fresh herbs right at the end.