Bring a large pot of salted water to a boil. Cook the pasta 2 minutes less than package directions for al dente. Drain and immediately toss with 2 tablespoons olive oil, 1 tablespoon vinegar, and a generous pinch of salt and pepper. Spread on a sheet tray to cool.
While the pasta cools, soak the diced red onion in cold water for 10 minutes, then drain well.
In a small bowl, whisk together mayonnaise, buttermilk, remaining vinegar, Dijon mustard, garlic powder, and cayenne. Taste and adjust seasoning.
In a large bowl, combine cooled pasta, cubed cheddar, drained red onion, diced bell pepper, celery, and cucumber.
Pour the dressing over the mixture and fold gently with a rubber spatula until evenly coated. Cover and refrigerate for at least 1 hour.
Before serving, taste for salt and pepper. Fold in fresh dill and parsley. If dry, add a splash of buttermilk or lemon juice.