Adjust rack to middle position and preheat oven to 425 degrees. Wash and dry produce.

Cut potatoes into ½-inch-thick wedges. Toss on a baking sheet with a large drizzle of oil, salt, and pepper.

Roast on middle rack until browned and tender, 20-25 minutes.

Meanwhile, thinly slice tomato into rounds.

In a small bowl, combine mayonnaise, mustard, 1 tsp water, ½ tsp garlic powder, and ½ tsp Old Bay Seasoning (2 tsp water, 1 tsp garlic powder, and 1 tsp Old Bay Seasoning for 4 servings). Set aside until ready to use in Step 4.

In a large bowl, combine beef*, ½ tsp Old Bay Seasoning, and ¼ tsp Worcestershire sauce (1 tsp Old Bay Seasoning and ½ tsp Worcestershire sauce for 4 servings). (Save any remaining Old Bay Seasoning and Worcestershire sauce for another use!)

Form beef mixture into two patties (four patties for 4), each slightly wider than a burger bun. Season lightly with pepper.

Heat a drizzle of oil in a large pan over medium heat. Add patties and cook until browned and cooked to desired doneness, 3-5 minutes per side.

In the last 1-2 minutes of cooking, top each patty with cheddar; cover pan until cheese melts.

While burgers cook, halve corn crosswise (skip if pre-halved). Wrap corn in damp paper towels. Microwave until kernels have softened and corn is cooked through, 3-4 minutes. Let rest for 1 minute.

Halve and toast buns until golden.

Spread a thin layer of Old Bay aioli on cut sides of bottom buns. Top with patties, tomato slices, and top buns.

Divide burgers, corn, and potato wedges between plates. Serve with remaining aioli on the side for dipping.