Combine the flour and pepper in a bowl, add the beef, and toss to coat well.
1/2 cup Flour, 1/2 tsp Ground black pepper
Heat the oil in the Dutch oven on medium-high. Add the beef a few pieces at a time; do not overcrowd. Cook, turning the pieces until beef is browned on all sides, about 5 minutes per batch; add more oil as needed between batches. 2 lbs Beef stewing meat, 1" cubes, 2-1/2 Tbsp Olive oil
Remove the beef from the pot and add the vinegar and wine. Cook over medium-high heat, scraping the pan with a wooden spoon to loosen any browned bits.
4 Tbsp Red wine vinegar, 2 cups Red wine
Add the beef, beef broth, and bay leaves. Bring to a boil, then reduce to a slow simmer. Cover and cook, skimming broth from time to time, until the beef is tender, about 1½ hours.
40 oz Beef broth, 4 ea Bay leaves
Add the onions and carrots and simmer, covered, for 10 minutes.
2 ea Onions, chopped, 10 ea Carrots, 1/4" rounds
Add the potatoes and simmer until vegetables are tender, about 30 minutes more.
4 ea Potatoes, 3/4" cubes, 3 tsp Salt
Add broth or water if the stew is dry. Season with salt and pepper to taste.