Heat a skillet over medium-high heat. Toast dried chiles, turning occasionally, until blistered, about 3-5 minutes. Add 1 cup water to cover chiles, bring to a simmer, cover, and cook for 5 minutes. Drain.

Combine chiles, achiote, garlic, chipotles, 2/3 cup onion, orange juice, vinegar, oil, cumin, brown sugar, and salt in a blender. Blend until smooth, about 30 seconds. Reserve 1/2 cup marinade and refrigerate.

Place remaining marinade in a dish or resealable plastic bag, add chicken, and toss to coat evenly. Cover and refrigerate for 8-24 hours.

Soak wooden skewers in water for at least 30 minutes while chicken marinates.

Preheat oven to 400°F (200°C). Line a roasting pan or baking dish with foil.

Thread pineapple slice onto two skewers, place chicken pieces over slice, and end with pineapple. Repeat for all skewers.

Bake in the oven for 30 minutes. Flip skewers and brush with reserved marinade. Bake for another 30 minutes. Broil both sides for 3-5 minutes until crispy.

Heat tortillas in a skillet over high heat for 1-2 minutes per side until browned.