Prepare the strawberry syrup and set it aside.
In a small bowl, mix the softened cream cheese, powdered sugar, and vanilla extract until smooth and well combined.
Take one tortilla and butter one side of it. Sprinkle the buttered side with a mixture of sugar and cinnamon. Set aside.
Spread half of the cream cheese mixture over another tortilla. Place the buttered tortilla, buttered side up, on top of the cream cheese spread, forming a sandwich.
Heat a pan or griddle over medium heat. Place the quesadilla, butter side down, onto the heated surface. Spread butter and sprinkle cinnamon and sugar on the top side. Cook until the bottom is golden brown, then carefully flip the quesadilla. Cook until the other side is also golden brown.
Remove the quesadilla from the heat and repeat the process to make the second quesadilla.
Slice each quesadilla into quarters or eighths. Top with the homemade strawberry syrup and a dollop of whipped cream, if desired.
Serve warm and enjoy!