Bring a large pot of salted water to a rolling boil over high heat, then add the rotini pasta and cook according to package directions until al dente, about 8-10 minutes.
While the pasta cooks, whisk together mayonnaise, sour cream, milk, white vinegar, sugar, salt, black pepper, garlic powder, and onion powder in a large mixing bowl until the dressing is smooth and fully combined.
Drain the cooked pasta in a colander and rinse under cold running water until completely cooled, shaking the colander to remove excess water.
Add the cooled pasta to the dressing bowl along with cubed cheddar cheese, halved cherry tomatoes, diced red onion, chopped fresh dill, and sliced black olives.
Gently fold all ingredients together using a large rubber spatula until the pasta is evenly coated with dressing and all components are distributed throughout.
Cover the bowl with plastic wrap and refrigerate for at least 1 hour before serving to allow flavors to meld and the salad to chill thoroughly.