Slice the tomatoes into ¼ inch thick slices and place into a sautee pan over high heat with 2 tablespoons vegetable oil. Sprinkle with salt and pepper. Do not overlap the tomatoes, and only put a single layer in at a time. Cook for 2 minutes per side. Remove from heat and set aside.
Once oven is ready, brush the flatbreads evenly with the melted garlic and butter mixture and place on a baking tray into the oven for 5 minutes.
As the flatbreads warm, shred the Mozzarella and Monterey Jack Cheeses.
After 5 minutes in the oven, carefully remove the flatbread and layer the tomatoes across the tops, then sprinkle heavily with both cheeses.
Then, place back into the oven for 3-5 minutes, or until cheese is completely melted.
Once melted, remove from oven, sprinkle with salt and pepper, and then generously top off the dish with a large portion of the tossed arugula.
Serve whole, or sliced, and enjoy!