In a medium bowl, combine the sliced strawberries and granulated sugar. Stir in 1 teaspoon of vanilla extract and let the mixture sit for about 15 minutes to macerate and release juices.
In a separate bowl, beat the softened cream cheese, powdered sugar, lemon juice, and 1/2 teaspoon of vanilla extract until smooth and creamy.
Lay a flour tortilla flat on a clean surface. Spread a generous layer of the cream cheese mixture over the tortilla, leaving a small border around the edges.
Spoon some of the macerated strawberries over the cream cheese layer, then add a dollop of whipped cream on top.
Carefully roll the tortilla tightly, starting from one end and rolling to the other. Repeat with the remaining tortillas and filling.
Once all tortillas are rolled, place them seam-side down on a serving platter. Refrigerate for at least 30 minutes to set.
Before serving, slice each roll into bite-sized pieces and sprinkle with graham cracker crumbs for added texture.