In a large saute pan over medium heat, cook the bacon until golden brown and crisped, about 4 minutes on each side. Transfer to a paper towel-lined plate.
Form the ground beef into 4 patties, about 3 1/2 inches in diameter. Sprinkle both sides of each patty liberally with salt and pepper.
Heat a grill, grill pan or cast-iron skillet over high heat, adding the canola oil if applicable. Cook the patties for approximately 3 minutes, then flip and top with the blue cheese crumbles (cover to melt). Continue cooking for an additional 3 minutes for medium, or continue cooking to your desired doneness.
Build the burgers by placing each cooked patty on the bun bottoms. Top with the bacon and smear the top buns with the Caramelized Onion Tomato Jam and place on top of the other ingredients. Serve immediately.
In a high-sided saute pan with a lid, heat the olive oil over medium heat. Add the onions, season with the salt, cover and cook until they are wilted and soft, about 10 minutes. Remove the lid and cook the onions until they are golden and caramelized, stirring often, another 20 minutes.
Stir in the garlic and saute, 1 to 2 minutes. Add the tomatoes and cook an additional 10 minutes. Add the molasses, sugar, vinegar, allspice, chipotle powder and cinnamon. Bring to a boil, and then reduce the heat to a simmer. Cook the jam, stirring constantly, until the tomatoes breakdown and the jam becomes thick, about 20 minutes.