Peel two sweet potatoes and quarter them. Place in a medium saucepan with two whole garlic cloves. Cover with water and bring to a boil. Simmer 10 to 15 minutes.
Drain and puree in a food processor with 3 tablespoons of butter, 1/2 teaspoon of salt and 1/4 teaspoon of ground pepper. Set aside.
Preheat oven to 450 degrees. In a large saute pan, lightly brown eight slices of Canadian bacon in 1 tablespoon of olive oil. Remove to a cutting board and cut into wedges. Cut eight slices of pineapple into similar-sized triangles. Spread the sweet-potato puree over four six-inch Italian-style flatbread crusts. Arrange pineapple and bacon pieces on crusts and sprinkle with 1/2 cup mixed shredded cheddar and Monterey Jack cheeses. Bake 10 to 15 minutes until golden-brown. Cut pizzas into wedges and serve.