Heat oven to 425F.
In a nonstick skillet, brown the beef breaking up into very small pieces as the meat cooks. Drain well.
Coat the potatoes evenly with the olive oil. Bake at 425F for 25 minutes or until cooked through. Remove from the oven and set aside until cool enough to handle.
Using a very sharp, straight-edged knife, slice each potato in half. Use a spoon or mellon baller to carefully scoop out the flesh leaving a 1/4- to 1/2-inch thick skin (the actual skin of these potatoes is very thin, so some of the flesh has to remain to make the stuff-able potato "skin"). Reserve 1 cup of the scooped out potato flesh.
In a medium bowl, mash the reserved potato with the milk. Add the remaining ingredients for the Cheeseburger Filling and combine.
Heat oven to 400F.
Place the potato skins on a bake sheet, hollowed side up. Spray lightly with cooking spray. Fill each skin with Cheeseburger Filling. Bake at 400F for 15-20 minutes until potato edges are lightly browned.
Remove from the oven, and let cool 5 minutes. Top each potato skin with a dollop of Dean's cheddar Bacon Dip. Garnish with snipped chives and serve. Yields: 30 bites.