Prepare vegetables: Peel cucumbers partially or fully, then slice into 1/4-inch rounds. For extra crispness, lightly salt the cucumbers with about 1/2 tsp for 15-20 minutes, then blot dry. Thinly slice the red onion and halve the cherry or grape tomatoes.
Make homemade ranch dressing: In a medium bowl, whisk together mayonnaise, sour cream (or Greek yogurt), buttermilk, and lemon juice. Add garlic powder, onion powder, dried dill weed, dried parsley flakes, any optional dried chives, salt, pepper, and an optional pinch of sugar. Whisk until smooth. Cover and chill for at least 30-60 minutes.
Cook beef bacon: Cook thick-cut beef bacon until crispy (bake at 400°F for 15-20 minutes or pan-fry). Drain on paper towels, then crumble into bite-sized pieces once cooled.
Prepare add-ins: Shred the sharp cheddar cheese and finely chop the fresh dill and fresh chives, preparing these for the salad.
Assemble the salad: In a large mixing bowl, combine the prepared cucumbers, red onion, and halved tomatoes. Toss in crumbled beef bacon and sharp cheddar cheese.
Dress, toss, and serve: Retrieve the chilled ranch dressing from the fridge. Pour about two-thirds of the dressing over the salad and gently toss until everything is coated. Fold in chopped fresh dill and chives, chilling for best flavor before serving.
Notes
For extra crunch, salt cucumbers beforehand. Dress salad just before serving to maintain freshness.