Heat olive oil in a skillet over medium heat. Add ground beef, season with salt and pepper, and cook for 6–8 minutes, breaking it up as it browns. Set aside.
In a separate skillet, cook the bacon over medium heat until crispy. Let it cool slightly, then crumble into small pieces.
Melt butter in a small saucepan over medium heat. Add heavy cream and bring to a simmer. Stir in shredded cheddar, garlic powder, paprika, salt, and pepper. Stir until smooth and creamy, then remove from heat.
Warm the tortilla in a dry skillet for 30 seconds on each side. Layer the center with cooked beef, crumbled bacon, shredded cheddar, lettuce, tomatoes, pickles, and onions.
Fold in the sides of the tortilla, then roll tightly to seal in all the fillings. Drizzle the creamy cheese sauce over the top or serve on the side for dipping.