In medium bowl, stir together olive oil, lemon juice, garlic, oregano and crushed red pepper. Season to taste with salt and pepper. Stir octopus into marinade; let sit at about 15 minutes.
Alternately thread octopus and chorizo onto 8 pre-soaked wooded skewers, allowing marinade to drip down onto chorizo; set aside.
In medium bowl, stir together pomegranate, cucumber, red onion, jalapeño and cilantro until well combined. Stir in olive oil and lemon juice. Season to taste with salt and pepper; set aside.
Heat grill or grill pan over medium-high heat. Place skewers on hot, greased grill grates. Cook, flipping once, until chorizo and octopus are heated through and develop golden-brown grill marks, about 5 minutes. Transfer skewers to serving platter; top with reserved pomegranate salsa. Serve.