Preheat the oven to 350 degrees. Rinse and pat dry the chicken breasts, place on a baking sheet, drizzle with olive oil and sprinkle liberally with salt and pepper. Roast for 35 minutes, until internal temp reaches 165 degrees. Set aside to cool.
When the chicken has cooled, remove the skin and bones, and shred the meat into small pieces by hand. Combine the torn chicken with the Frank's Red Hot and 2 Tbsp of sour cream, along with a pinch each of salt and pepper. Set aside for assembly.
Make the Ranch - combine all ingredients and stir together into a smooth consistency. This will make WAY more than you need, but it's great to serve along side and use for veggies afterwards.
To assemble the Quesadilla's, lay the tortilla out on a cutting board, and cut one slit into the center of the disc. You are working with four quadrants, and you want both of the outside pieces to have cheese for melting, so place ingredients as pictured, in the following order. Lower left, chicken and sprinkle with chopped chives; upper left, a smear of ranch, topped with chopped lettuce, scallions and cilantro. Upper right, a slice of Pepperjack cheese; lower right a combination of grated cheese.
Fold the wrap up into one triangle with four layers - starting with the lower left, fold the chicken up over the romaine and ranch, then fold over to the top right, and finally lower right. You will have a wedge of stacked quesadilla to pan fry and melt the cheese.
In a cast iron or non-stick skillet over medium heat, coat the pan with olive oil, and sear the outsides of the wrap on both sides, taking care to keep all ingredients tucked inside safely. Serve alongside with extra ranch and a drizzle of Frank's, with chopped chives and cilantro to top.