In a medium bowl, combine the flour and pepper. Add the beef cubes and toss until evenly coated, shaking off any excess flour.
Heat about 3 teaspoons of avocado oil in a large Dutch oven or heavy-bottomed pot over medium-high heat. Working in batches, add the beef in a single layer and brown on all sides, about 5 minutes per batch. Transfer the browned beef to a plate and add more oil as needed between batches.
Pour the red wine vinegar and red wine into the same pot. Use a wooden spoon to scrape up the browned bits from the bottom as the liquid comes to a gentle simmer.
Return the beef to the pot and pour in the beef broth. Add the bay leaves and fresh thyme. Bring everything to a boil, then reduce the heat to low. Cover and gently simmer for about 1½ hours, or until the beef is fork-tender (check at an hour).
Stir in the carrots, cover, and simmer for 10 minutes. Add the potatoes and continue cooking for about 30 minutes, or until the potatoes and carrots are tender.
Remove the bay leaves and thyme stems. Taste the gravy and adjust the salt and pepper as needed. If the stew gets thicker than you'd like, stir in a little extra beef broth or water. Serve warm with buttered Hawaiian rolls for dipping!