Pat the shrimp very dry with paper towels and place into a bowl.
In a bowl or jar, whisk or shake the olive oil, maple syrup, chipotle chili powder, smoked paprika, garlic, cilantro, and a pinch of salt and pepper. Pour half of the marinade over the shrimp and toss to coat. Let sit 10-15 minutes at room temperature.
Thread the shrimp and pineapple chunks onto skewers, alternating the two as you please. Or, do whole skewers or just shrimp or just pineapple. Whatever floats your boat.
Preheat your grill or grill pan to medium high. Add the skewers and grill for 2-3 minutes per side until nicely charred. Move to a plate and baste with the reserved chipotle sauce. Repeat with remaining skewers.
To make the ranch, combine the yogurt, mayonnaise, cilantro, dill, garlic, onion, jalapeno, lemon juice, and buttermilk. Add more buttermilk if you desire a thinner consistency. Season to taste with salt and pepper.
Serve the skewers warm with rice, leftover chipotle sauce, and ranch.