Pre-heat oven to 400°F and line a large, rimmed baking sheet with parchment paper or a Silpat baking mat. Set aside.
Heat one tablespoon olive oil in a large skillet over medium-high heat. Add the pork chops and sear on both sides, approximately 1-2 minutes per side. Season with salt and black pepper, to taste, on each side while cooking.
Remove from heat and transfer the browned pork chops to the prepared baking sheet. Place in the pre-heated oven to roast until cooked through, approximately 12-15 minutes.Tip: Check for doneness after 10 minutes and adjust final cook time accordingly. (An instant-read thermometer inserted at the thickest point should read 140°F when ready. The internal temperature will continue to rise another 5°F while the pork chops rest).
Once the pork chops are in the oven, combine the vinegar, maple syrup, garlic, rosemary, and red pepper flakes in a small saucepan over medium heat. Season with salt and black pepper, to taste, and cook, stirring occasionally, until slightly thickened, approximately 4-5 minutes. Reduce heat to low and continue to simmer, stirring occasionally, until ready to serve.
Meanwhile, add the remaining olive oil and the sliced peppers to the skillet used to sear the chops and place over medium-high heat. Season with salt and black pepper, to taste. Cook, stirring occasionally, until the peppers soften and develop a bit of color, approximately 6-8 minutes.
Add the pineapple and continue cooking until heated through, approximately 2-3 minutes. Stir in the green onion and parsley, and remove from heat.
Remove pork chops from oven. Cover loosely and let rest for 5 minutes. To serve, pour the glaze over the pork chops and serve alongside the peppers and pineapple.
Store leftovers in the refrigerator, tighly covered, for up to 3 days.