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In a heatproof bowl, combine all the chilies; cover with boiling water. Let stand until softened, 15 to 20 minutes. Reserve ¼ cup of the water, then drain. Meanwhile, halve the pineapple lengthwise, then cut each piece crosswise ¼ inch thick.
In a blender, puree the chilies, reserved water, ½ cup pineapple slices, garlic, oil, sugar, cumin, oregano, 1½ teaspoons salt and 1 teaspoon pepper on high until smooth, 1 to 2 minutes. In a medium bowl, toss the sauce with the pork to coat.
Heat the oven to 500°F with a rack in the upper-middle position. Line a rimmed baking sheet with foil and spread the pork in an even layer. Arrange the remaining pineapple over the pork. Roast until the pineapple is spotty brown and the pork is crisp at the edges, 25 to 30 minutes. Transfer to a cutting board and chop the pork and pineapple together into bite-sized pieces. Taste and season with salt and pepper, then serve with corn tortillas and desired toppings.