Season beef pieces generously with salt and pepper, then dredge each piece in flour. Sear off in a large soup pot with a little oil to brown outsides, then remove from heat and set aside.
In the same pot, heat 2 tbsp. oil and saute chopped onion until translucent. Add carrots, 1 tsp salt, garlic, oregano, and cabbage. Cook and stir until veggies become tender and fragrant.
Add broth, crushed tomatoes, water and beef. Bring to boil and turn down heat to medium, cook 15 minutes, stirring occasionally.
Add barley, cook for another 35-45 minutes until barley is soft and cooked through. (Stir occassionally so that the barley doesn't stick.) Add more salt and pepper to taste. Add water as necessary for desired consistency.