Preheat the oven to 475°F. Prepare one or two baking sheets for oven-roasting the burgers by lining each with foil and placing an oven-safe non-stick cooling or grill rack inside. Sprinkle salt in the baking sheet to soak up drippings while cooking and prevent the grease from smoking. Set aside.
Meanwhile, prepare the pineapple and bacon. Break down a fresh pineapple and cut it into ½ inch thick rings, removing the tough center with a knife or round cookie cutter. Reserve half the rings for another use, and pat dry the rings to be used as toppings with paper towels. Heat a large non-stick skillet over medium heat, and add the tablespoon butter. When it’s melted (do not let it brown), sauté the pineapple rings in batches until caramelized, about 3-5 minutes per side. Remove the pineapple rings to a plate and cover to keep warm. Once the pineapple is finished, move on to the bacon. Using the same skillet, pan-fry the bacon in batches until just crisp. Remove from heat to a plate (separate from the pineapple) and cover to keep warm.
Once the oven is at temperature, gently combine the ground beef with the salt and pepper in a large bowl. Be careful not to over-mix, as this may cause the meat to become tough once cooked. Form the seasoned meat into patties that will fit nicely on your rolls, about 2-3 inches in diameter. Arrange the patties on the prepared baking sheets. Cook in the oven for about 4 minutes on each side for medium-rare, melting the slices of cheese 1 minute prior to desired doneness. You can cut samples open, or check the temperature of your burgers with a thermometer: 130-135°F for medium rare, 140-145°F for medium.
Finally, assemble the ingredients. Break (or cut) the crispy bacon into pieces the size of the buns and cut the pineapple rings into 1-inch wedges or segments. Spread steak sauce on the bottom bun of each burger, then top with bacon, cheeseburger patties, pineapple wedge, and one or two candied jalapenos, in that order. Cover with the top buns and secure the ingredients together with a toothpick. Arrange on a big tray and serve to happy guests before you eat them all yourself.