1: Heat a large skillet over medium heat and melt the butter. Add the bacon, shallot, mushrooms, poblano, and celery and saute until the bacon is crisp and the vegetables are soft. Stir in the panko, lemon zest, and parsley. Season to taste with salt and pepper. Let cool.
2: Remove the tentacles, but leave the cluster intact. Spoon the stuffing into the squid bodies until full. Plug with the tentacle cluster, then pin shut with bamboo skewers or toothpicks. (Trim off any excess wood.) Drizzle the stuffed squid with extra virgin olive oil. Season with salt, pepper, and oregano.
3: Prepare the pepper kebabs: Thread skewers (metal or bamboo) with shishito peppers, prunes, and bacon. Repeat.
4: Set up your grill for direct grilling and heat to medium-high. Brush or scrape the grill grate clean and oil with vegetable oil. Arrange the stuffed squid and pepper kebabs on the grill grate. Grill for 2 to 3 minutes per side, turning with tongs. Serve immediately.