Heat a medium soup pot over medium-high heat. Add 2 tablespoons extra-virgin olive oil, 2 turns of the pan and the jalapenos, bell pepper, onions, celery and garlic. Season with salt and pepper then saute veggies 5 minutes, add tomatoes, crushed tomatoes and stock and bring soup to a bubble. Reduce heat to a simmer and stir in cilantro.
Paint 1 side of 2 tortillas with oil and place them next to each other, oiled side down, on a large cookie sheet. Mix cheddar with scallions and divide the cheese between the tortillas evenly. Top with another tortilla and top each of those with equal amounts of Pepper Jack cheese. Set the last tortillas on top and brush tops with extra-virgin olive oil. Cook 10 minutes in the oven to melt cheese and crisp up tortillas. Cool quesadillas 5 minutes to set then cut each quesadilla into 6 pieces.
Serve bowls of stoup with 3 wedges quesadilla along side each bowlful. Pass the Avocado Smash and the sour cream for topping soup or quesadillas.
Remove 1 avocado flesh to a bowl. Add the cilantro and scallions. Pop the lime in the microwave for a few seconds. Add the juice of 1 lime, the sour cream, and season with salt and pepper. With a fork or spoon, smash up the mixture, leaving chunks for a good consistency.
Chop and seed the plum tomato and fold into avocado. Serve.