In a medium-sized bowl, place the stew meat, flour, 1 ½ tsp salt, and 1 tsp pepper. Toss to combine until all pieces of meat are well covered with flour
Heat two tbsp olive oil in a large dutch oven (or oven-proof pot) over medium-high heat and brown the meat on all sides (you might need to work in batches). Transfer to a plate and reserve
Pour 2 cups of red wine into the Dutch oven and bring to a boil. Make sure you scrape the bottom of the pot to pick up all the brown bits and pieces (they provide lots of flavors). Reduce the heat to low, add the mushrooms, and simmer for about 10 minutes
Heat ½ tablespoons of olive oil in a large skillet, over medium-high heat, and saute the onions, garlic, and sliced onions until the onion is translucent about 4 minutes. Add 1 tbsp tomato paste and cook for one more minute. Transfer these veggies to the pot
Add beef broth, bay leaves, dried thyme, dried rosemary, 1 tsp salt, and ½ tsp pepper to the pot. Return the beef, add the diced potatoes, and stir to combine. Place the lid on and bake at 325 F for 1 hour and 45 mins. Check the seasoning and adjust if you feel it needs more salt, and if you want it thicker, dissolve two teaspoons cornstarch in ¼ cup water, add it to the pot, and simmer for 5 minutes until thick.