Preheat the oven to 375°F.
Cut 2.5-inch circles out of the tortillas (3 per tortilla). Brush the circles with olive oil on both sides.
Place the tortilla circles in mini muffin pans. Sprinkle with salt and pepper and bake until golden, approximately 6 minutes. Let the shells cool. Cover them in an airtight container until ready to use.
In a medium pot over high heat, bring 3 quarts of water to a boil. Add a generous pinch of salt to flavor the pasta. Add the pasta, stir, and simmer for approximately 8 minutes, or according to the directions on the package. Once the pasta is cooked, drain into a colander, then lay it out flat in a
shallow pan to cool down to room temperature, about 10 minutes.
Add the canola oil and stir it through the pasta to avoid clumps.
Fill a medium pot one-third of the way up with water. Place a larger stainless bowl over the pot; set on medium. Add the milk or half-and-half and allow it to heat up. Add the cheeses in handfuls and stir with a wooden spoon, until all the cheeses are melted. Check the consistency. If it is too thin and won’t stick to the pasta, add more cheese. Add a bit more milk if it appears to be too thick.
Stir in the teaspoon of chipotle puree, add salt, and adjust seasonings if needed. Add the pasta. Stir to heat through.
Spoon the macaroni into the mini taco shells and garnish with guacamole and additional chipotle purée on top.
Serve on a decorative platter (be sure not to set out too early, as taco shells might get soggy) or pass as a small bite.