Heat oven to 375°F. Grease a 9x13-inch baking dish.
Place potatoes in a pot and cover with cold salted water. Boil, then simmer until tender, 12–15 minutes.
Warm olive oil in a skillet over medium heat. Soften onion 4–5 minutes. Stir in garlic 30 seconds. Cool slightly.
Drain potatoes well. Return to the pot. Add butter, milk, sour cream, and half the salt and pepper.
Mash until smooth and creamy. Set aside.
Combine beef, breadcrumbs, mayonnaise, Worcestershire, Dijon, 2 tbsp ketchup, oregano, and paprika in a large bowl.
Add remaining salt and pepper, the onions and garlic, and 3/4 cup cheddar. Mix gently until just combined.
Press meat mixture into the baking dish in an even layer. Spread remaining ketchup over the top.
Bake 30 minutes, until the edges begin to brown.
Spread mashed potatoes over the meatloaf. Sprinkle remaining cheddar evenly on top.
Bake 15–20 minutes more, until cheese melts and center hits 160°F. Broil 2–3 minutes to brown, if desired.
Rest 10 minutes. Garnish with parsley, slice, and serve warm.