Bring a large pot of generously salted water to a rolling boil over high heat.
Add the rotini pasta and cook according to package directions until al dente, typically 1 to 2 minutes less than the package suggests.
Drain the pasta immediately through a colander, then rinse under cold running water for 60 to 90 seconds, tossing gently, until cooled to room temperature.
Spread the rinsed pasta in a single layer on a large baking sheet or toss with a small drizzle of olive oil if holding for more than a few minutes.
In a medium mixing bowl, combine the mayonnaise, sour cream, ranch seasoning packet, garlic powder, and onion powder, then whisk until completely smooth.
Add the milk and whisk again to loosen the dressing slightly; taste and adjust with lemon juice or apple cider vinegar if more zip is needed.
Wash and dry all vegetables, then halve the cherry tomatoes, dice the cucumber and green bell pepper into 1/4-inch pieces, and finely dice the red onion into 1/8-inch pieces.
Cut the sharp cheddar into 1/2-inch cubes or shred it on the large side of a box grater, and drain the black olives thoroughly, patting dry with a paper towel.
Transfer the cooled rotini to a large mixing bowl and add the cherry tomatoes, cucumber, red onion, green bell pepper, cheddar cheese, and drained black olives.
Pour the entire ranch dressing over the top and gently fold everything together from the bottom of the bowl upward until evenly coated.
Season with salt and black pepper to taste, starting with 1/2 teaspoon of salt and a few cracks of pepper, then adjust as needed.
Cover tightly with plastic wrap or transfer to an airtight container and refrigerate for at least 1 hour, preferably 2 hours, to let the flavors meld.
Before serving, stir well and add 1 to 2 tablespoons of additional mayonnaise or a splash of milk if the salad looks dry, then taste and adjust seasoning.
Garnish with freshly chopped dill or chives if desired and serve chilled.