Step 1: Preheat oven to 350F.
Step 2: Oil 13x9x2-inch roasting pan.
Step 3: Heat 2 tablespoons oil in large nonstick skillet over medium-high heat. Add onions and sugar; saute until onions are deep golden brown, about 15 minutes. Stir in oregano and garlic. Add vinegar; cook until evaporated, about 2 minutes. Transfer to large bowl and cool.
Step 4: Add ground beef, pork, 1 cup crushed tomatoes and next 6 ingredients to onions. Mix with fork until just blended.
Step 5: Form meat mixture into 10-by-5-inch loaf shape in prepared pan.
Step 6: Bake 45 minutes.
Step 7: Spread remaining crushed tomatoes over meat loaf. Drizzle with 1 tablespoon oil.
Step 8: Bake until thermometer inserted into center registers 155F, about 1 hour. Cool 15 minutes.
Step 9: Meanwhile, heat 2 tablespoons oil in large skillet over medium-high heat. Add mushrooms; saute until tender, about 12 minutes. Season to taste with salt and pepper.
Step 10: Cut meatloaf into thick slices.
Step 11: Spoon mushrooms and pan juices over.
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