Mix the hamburger, egg, onion, crumbled bacon,crushed Ritz crackers, salt and pepper, salad dressing, 1/4 c. of the brown sugar and milk together in large bowl.
Arrange meatloaf in pan of choice. *NOTE: I use a large glass baking dish and arrange it in an "O" shape. That way it doesn't take the middle so long to cook.
Mix ketchup and the remaining 1/4 c. of brown sugar and "glaze" the top of the meatloaf.
Bake for 45-1 hour. Meatloaf is done when the inside is no longer pink, and has an internal temp of 160*
*NOTE: I don't usually measure things so the amounts are approximate. If something seems a little off, please feel free to adjust it. If it's too sweet for your liking omit the brown sugar inside the meatloaf