Place tomatoes on one side of a large, rimmed baking sheet. Place the onion on the other side of the baking sheet. Drizzle with 1 1/2 tablespoons olive oil, season with 1/4 teaspoon salt and 1/4 teaspoon black pepper, toss to coat; spread each out into a single layer. Place the garlic onto a double thickness piece of foil, drizzle with 1/2 tablespoon of olive oil, seal foil tightly around garlic cloves. Place onto baking sheet next to the tomatoes and onions. Place baking sheet into preheated oven and cook for 25 minutes, until veggies have softened. Remove from oven and cool slightly.
Finely chop tomatoes and onion, place into a medium bowl. Remove garlic from skin and mash, add to bowl. Add in the lemon zest, 1 teaspoon lemon juice, vinegar, 1/4 teaspoon salt and remaining 1/8 teaspoon black pepper, mix to fully combine; set aside.
In a small bowl, place the cream cheese, bleu cheese and horseradish; mix to fully combine; set aside.
In a small bowl, mix together the cayenne pepper, remaining 1/4 teaspoon salt, garlic powder, and ancho chili powder. Rub spice mixture evenly onto steak. Heat remaining 1 tablespoon olive oil in a non-stick grill pan or skillet over medium-high heat. Add in the steak and cook to desired doneness, approximately 5 minutes per side for medium. Remove from pan to a medium platter, cover with aluminum foil, let rest for 3 minutes. Using a pastry brush, brush the raspberry jam onto both sides of the steak, re-cover and let rest an additional 2 - 3 minutes. Slice steak into thin slices, against the grain.
In a small bowl, place the extra virgin olive oil, remaining 1 teaspoon lemon juice and crushed red pepper flakes, whisk together. Add in the baby greens, toss to coat.
Heat flat bread according to package directions. Evenly spread the bleu cheese/horseradish spread evenly over the flat breads. Evenly divide the steak between the flat breads, but only cover 1/2 of each flat bread, (drizzle steak slices with a little of the melted jam). Top the steak evenly with the tomato jam and the baby greens. Fold the uncovered half of the flat bread over the covered half. Secure with tooth picks and enjoy.