Pre-heat a large skillet over medium-high heat and add 1 tbsp of olive oil.
While the skillet is pre-heating, pat the steak dry and coat it evenly with 1 tbsp olive oil followed by the Montreal Steak Seasoning.
Place the steak in the skillet and grill for 6-7 minutes per side or until your preferred temperature is reached.
Let rest for 10 minutes before dicing.
Peppers and Onions:
While the steak is resting, add the peppers and onions to a large mixing bowl and evenly coat with olive oil. Add the garlic powder and salt and mix to evenly coat.
Wipe the skillet clean. Add the peppers and onions to the pre-heated skillet and saute approximately 5 minutes, until golden brown. Transfer to a plate and set aside.
Make the Quesadilla:
Turn the temperature of the skillet down to medium heat.
Place the tortilla on a flat surface and build the layers: To one side of the tortilla add 1/4 cup of cheese, 1/4 cup diced steak, 1/4 of the onion and pepper mix and 1/4 cup cheese. Fold the tortilla in half ensuring the edges line up.
(*Note 1) Carefully transfer the quesadilla to the skillet and cook for 3-4 minutes per side, until the cheese is melted throughout. Remove from the heat and set aside.
Repeat until all the quesadillas have been cooked.
Slice each quesadilla in half and top with your favorite toppings.
Notes
Note 1 - For an extra crispy crust, add 1/2 tbsp of butter to the skillet (let melt) before adding the quesadilla to cook. Repeat between batches.