Preheat oven to 375°F***. Line a cookie sheet with parchment paper and grease any exposed areas with a light coating of butter or canola oil. Set aside.
In a small bowl, whisk together the flour, cocoa powder, baking soda, and salt. Then, whisk the sour cream, whole milk, and vinegar in a liquid measuring cup until combined.
In a large bowl, cream the butter and sugar until light and fluffy, 2-3 minutes. Add the eggs one at a time followed by the vanilla extract, canola oil, and red food coloring. Add half of the flour mixture followed by half of the milk mixture until just combined. Repeat with the remaining flour and milk mixtures. The batter will be thick.
Spread the red velvet cake batter into the prepared pan, ensuring that the batter is evenly distributed. Bake, checking for doneness at 8 minutes. The cake is ready when an inserted toothpick has just a few moist crumbs. Let the cake cool in the pan for about 5 minutes. Then, use the parchment paper to transfer the cake to a cooling rack, and let cool completely.
While the cake is baking, use a stand mixer or hand mixer to beat the butter and powdered sugar together in a medium bowl until light and fluffy. Mix in the vanilla extract.
Add the heavy whipping cream to the cream cheese mixture, and beat over medium-high until stiff peaks form. Taste, and add more powdered sugar if desired.
Have six glasses or jars ready. Once the cake is cooled, use a cookie cutter the same diameter of your glasses/jars to cut out 18 circles. Place one cake circle in the bottom of each glass/jar.
With a piping bag and tip, pipe a layer of cheesecake filling over the cake circles. Sprinkle each layer of filling with a scant Tablespoon of cookie crumbs. Repeat two more times so that you have three layers total in each glass.
To finish, top each cheesecake red velvet trifle with a strawberry. Enjoy!
*Use 1 tsp. of baking soda for sea-level baking. Use 1/2 tsp. for high altitude (~5,000 ft.)**Use 1/2 c. whole milk for sea-level baking. Use 1/2 c. + 2 Tbs. for high altitude (~5,000 ft.)***Bake cake at 350°F for sea-level. Bake cake at 375°F for high altitude (~5,000 ft.)I use standard 12oz drinking glasses as the vessel, which is the perfect size for 3 layers of cake/filling.