Cook the bacon in a 12-inch skillet over medium heat for 8 to 10 minutes, turning as needed, until crisp; transfer to a paper towel-lined plate.

Pour off the bacon drippings and carefully wipe the skillet; add the oil and potatoes, cover, and cook over medium-low heat for 8 to 10 minutes, stirring once or twice. Uncover and cook over medium-high heat for 5 to 7 minutes, stirring occasionally, until tender and golden; transfer to a plate.

Cook the sausage in the same skillet over medium heat for 6 to 8 minutes, breaking it into small pieces, until browned and it reaches 160°F; transfer to the plate with the potatoes.

Whisk the eggs, milk, salt, and pepper in a medium bowl.

Pour the egg mixture into the skillet and cook over medium-low heat for 2 to 4 minutes, stirring gently, until just set.

Warm the tortillas, covered with a slightly damp paper towel, in the microwave for 20 to 30 seconds to make them flexible.

Divide the potatoes, sausage, eggs, and crumbled bacon among the tortillas; top each with cheddar, fold in the sides, and roll up tightly.

Toast the burritos seam-side down in the skillet over medium heat, working in batches, for 1 to 2 minutes per side until golden and the cheese is melted.