Place the shrimp into a mixing bowl. Add 2 tablespoons of oil, 1 tablespoon of kosher salt, and the chile spice blend. Toss well. Cover and marinate in the refrigerator for 30 minutes. Transfer the bowl to room temperature and let sit for 10 minutes before grilling.
Meanwhile, heat the grill over high heat. Coat the jalapeño and pineapple slices with a drizzle of oil and a pinch of salt. Grill both for a few minutes until charred on all sides and tender. Remove from the grill. Peel the jalapeno and remove the stem. Chop it finely. Dice the pineapple, removing any hard core sections.
In a large mixing bowl, whisk together the lime juice, lime zest, red wine vinegar, honey, and garlic. Drizzle in the oil, whisking continuously. Season with a pinch of salt to taste. Set aside.
When the shrimp is ready, place it onto the grill and cook for a couple of minutes on each side until charred and pink. Allow to cool for a few minutes before assembling the salad.
Add the arugula, cherry tomatoes, avocado, radish, basil, pineapple, and shrimp to the bowl of vinaigrette. Toss well. Taste and season with more salt if needed. Serve immediately with lime wedges on the side.