First, prepare your cheese tortillas. Drizzle olive oil in a nonstick frying pan and heat over medium heat.
Place one slice of cheddar cheese into the pan and heat the cheese wrap until it begins to bubble and brown around the edges. It will start to melt immediately, but it will take around 4-5 minutes to get nice and crispy.
Remove the pan from heat and let the crispy cheese tortilla cool in the pan for 2-3 minutes. As it cools it will harden even more.
Carefully remove the crispy cheese tortilla from the pan with a spatula and set it on a plate. Repeat until all the tortillas have been made and hardened. Set aside.
Prepare your ground beef by heating a large skillet over medium/high heat.
When the pan is hot add ground beef. Using a wooden utensil, break the ground beef into small pieces. Let the beef cook for 3-5 minutes.
When the beef begins to brown*, add taco seasoning and water to the pan and mix until all of the ingredients are combined. Bring to a boil.
Once boiling, turn the heat to low and let simmer for 5-7 minutes in order to thicken the sauce.
The liquid should thicken and the beef should have absorbed most of liquid.
Before assembling quesadillas, make sure that all of the cheese tortillas have cooled enough to harden.
To assemble the quesadilla, spread 1 tablespoon of Greek yogurt and 1 tablespoon of guacamole on each crispy cheese tortilla.
Then, evenly distribute the ground beef, cherry tomatoes, red onion, and fresh cilantro on 2 of the cheese tortillas.
Top those ingredients with the other two cheese tortillas (Greek yogurt and guacamole side down).
Cut the quesadillas into quarters with a sharp knife in a flat, firm downward motion to avoid the cheese tortillas from cracking and enjoy!