Preheat the oven to 325°F (165°C). Line a 9×13-inch baking pan with parchment paper, leaving a slight overhang for easy removal.
Melt the chocolate chips in a medium bowl using the microwave in 20–30 second intervals, stirring between each until smooth.
Whisk in the coconut oil, sugar, coffee, eggs, and 1 teaspoon vanilla extract until well combined.
In a small bowl, mix together the gluten-free flour, cocoa powder, baking soda, and salt. Add the dry ingredients to the chocolate mixture and stir until fully incorporated.
Pour the brownie batter evenly into the prepared pan and set aside.
In another medium bowl, beat the softened cream cheese, sweetened condensed milk, lemon juice, and remaining 1 teaspoon vanilla extract using a hand mixer on medium speed until smooth and lump-free.
Dollop the cheesecake mixture over the brownie batter. Do not spread; allow it to sit in spoonfuls across the surface.
In a small bowl, crush the raspberries with a fork until they form a loose puree. (If needed, microwave the raspberries for 15–20 seconds to soften.)
Spoon the raspberry puree over the cheesecake dollops. Using a knife, gently swirl through all layers to create a marbled effect.
Bake on the middle rack for 40–45 minutes, or until a toothpick inserted into the center comes out mostly clean with just a few moist crumbs.
Cool completely on a wire rack before lifting from the pan and cutting into 2-inch squares.