Preheat oven to 375F (190C) and line a 12 count muffin tin with paper liners.
Cream Cheese Filling: Place cream cheese in a mixing bowl and stir until smooth. Add granulated sugar and vanilla and stir until creamy and completely combined. Set aside.
Muffins: In a medium-sized bowl, use an electric mixer to cream together softened butter and sugars until well-creamed.
Add eggs and beat until combined.
Stir in pumpkin puree and vanilla extract until combined, then add milk and stir well. Be sure to scrape down the sides and bottom of the bowl to ensure that all ingredients are well combined.
In a separate, medium-sized bowl, whisk together flour, pumpkin spice, cinnamon, baking powder, baking soda, and salt.
Using a spatula, gradually add dry ingredients and wet and stir until just combined — do not over-mix!
Portion about 2 tablespoons of pumpkin muffin batter into the bottom of each muffin liner. Use the back of a spoon to make a small crater/nest in the center of the batter.
Drop a heaping tablespoon of cream cheese filling into the nests you've created then drop/smooth more pumpkin muffin batter overtop, taking care to completely cover the cream cheese and filling liners ¾ of the way full.
Streusel: Whisk together flour, sugars, and ground cinnamon until combined.
Add melted butter and toss/claw together ingredients until clumpy.
Evenly divide streusel over pumpkin batter. Transfer muffins to 375F (190C) preheated oven and bake for 23-25 minutes or until tops are beginning to turn golden brown and a toothpick inserted in the center comes out with dry pumpkin muffin crumbs.
Allow to cool before serving.