Heat a smoker to 250°F. Cook 2 slices of bacon in a skillet until crisp. Set them on a paper towel to cool, then crumble them. Reserve the skillet for the beans.
In a large bowl, whisk the egg with the milk and 1 tablespoon of ketchup. Stir in the breadcrumbs, taco seasoning, salt, and black pepper. Add the ground beef, crumbled bacon, cheddar, onion, and jalapeño. Mix gently just until combined.
Shape the mixture into a compact loaf on a small piece of foil or in a shallow foil pan. Place it in the smoker and cook until the center reaches 160°F, checking with an instant-read thermometer.
While the meatloaf smokes, cut the remaining 2 bacon slices into small pieces. Cook them in the reserved skillet until crisp. Spoon off excess bacon fat, leaving about 1 teaspoon in the pan.
Add the pinto beans, tomato sauce, cumin, and chipotle powder to the skillet. Stir and simmer gently until the beans are hot and the sauce has thickened slightly. Keep warm until serving.
Brush the top of the smoked meatloaf with the remaining 1 tablespoon of ketchup during the last 10 minutes of cooking. Once it reaches 160°F, remove it from the smoker and let it rest for 10 minutes before slicing.
Serve the meatloaf with the chipotle beans and finish the beans with chopped cilantro.