Heat the olive oil in a large skillet over medium high heat. Add in the sausage and brown it as you break it up. It will take about 5 minutes to cook completely. While it is browning, pour in the dash of Worcestershire to flavor it more. Meanwhile, combine the eggs, milk, salt, pepper and sriracha in a bowl and whisk that all together thoroughly. Turn the burner heat to medium and pour the egg mixture over the cooked sausage. Stir it all constantly and let the eggs form soft, scrambled curds. Do not let the eggs dry out since they will cook more in the waffle iron. Take the pan off of the heat and set it aside.
Pre-heat a standard sized Belgian waffle iron. While it heats up, assemble the first quesadilla. Spread 1/4 of the egg mixture out evenly and tightly on one of the soft taco shells, then sprinkle a 1/4 cup of the shredded cheddar on top of it. Close the quesadilla with another soft taco shell on top. Butter the waffle iron generously to grease it, then firmly press the quesadilla in it. Let it cook for about 3 minutes. While it is cooking assemble the next quesadilla.
When the first quesadilla is done, take it out and lightly wipe down the waffle iron to clean up any mess. Butter it again before cooking the next one. Cut the quesadilla into quarters and serve it immediately with any desired dipping sauces. Ketchup, maple syrup or salsa all are perfect options! Repeat to make 4 quesadillas total and enjoy!