Preheat oven to 350° F. Prepare cupcake baking pan by lining with cupcake liners.
In large mixing bowl, or stand mixer with paddle attachment, beat butter and sugar until fluffy. Add vanilla and mix until combined.
Add eggs one at a time, mixing in between, until incorporated. Add vinegar, red wine, and buttermilk and combine.
In seperate mixing bowl, whisk together flour, cocoa powder, baking soda, and salt. Pour dry mixture into wet mixture and mix until just incorporated. Do not overmix.
Scoop evenly into prepared baking cups and bake at 350° F for 16-19 minutes or until toothpick inserted in center comes out clean. Cool completely on wire baking rack.
Frosting:
Beat together cream cheese, butter, powdered sugar, and vanilla until creamy. Stir in red wine and red food coloring.
Increase speed to high and slowly add in cream, then continue to whip until stiff peaks form.