Heat Wolf Gourmet Countertop Oven to Convection/Roast 450°F. Line the Wolf Gourmet baking pan with parchment paper. Coat pineapple in olive oil and arrange on baking sheet. Roast until tender and juices begin to release, 15-20 minutes. Let cool.
Using a Wolf Gourmet High-Performance Blender, combine avocado, sour cream, and freshly grated lime zest and juice from one lime. Purée to a smooth crema.
Heat a large skillet over medium-high. Season chicken with salt and pepper. Add 2 tablespoons vegetable oil to the pan and carefully swirl to coat. Arrange chicken in a single layer in the pan and cook, flipping once, until cooked through, 10-12 minutes. Transfer to a cutting board and let sit five minutes before slicing.
Chop roasted pineapple into small pieces. In a medium bowl, combine pineapple, cucumber, onion, and jalapeño. Season to taste with lime juice and salt. Serve with chicken tacos and avocado crema.