Combine the flour and pepper in a bowl, add the beef and toss to coat well. Heat 3 tsp of the oil in a large pot or dutch oven and add the beef a handful of pieces at a time - you don't want to overcrowd the pot. Cook about 5-6 minutes per batch, turning the pieces until beef is browned on all sides. Add more oil as needed between batches.
Remove the beef from the pot and add the wine and vinegar. Cook over medium-high heat, scraping up the browned bits in the pot with a wooden spoon. Add the beef, stock and bay leaves. Bring to a boil, then cover and reduce heat to maintain a slow simmer.
Cover and cook, skimming from from time to time, until the beef is tender, about 1 1/2 hours. Add the onions and carrots and simmer, covered, for 10 minutes. Add the potatoes and simmer with the cover off until vegetables are tender, about 30 minutes more. Add more stock or water if the stew is dry. Season with salt and pepper to taste.