Break each piece of cooked bacon into 5 pieces. This will give you enough bacon for each burger bite.
Combine ground beef with salt, pepper, and garlic powder.
If using the waffle potatoes, bake them according to the package instructions.
Shape all 20 pieces at once into round patties about 1" in diameter, making sure to flatten so the burger bite will be able to stand on a tray. Set aside.
Heat a nonstick frying pan over medium-high heat and place all burger bites into the pan at the same time.
Brown for about 3-4 minutes and flip each burger bite.
Top with the square pieces of cheese and continue to cook for another 3-4 minutes.
If the cheese is not melting, cover the pan for about a minute and remove the cover.
Remove the burger bites from the pan (place on waffle potatoes if using them), and plate on serving dish.
Top each bite with a small piece of bacon, a sliver of pepper or pickle, half of a grape tomato, and then slide the skewer in the middle of the tomato to secure.