Blistered Cheesy Peppers

Ingredients

• 1 large shallot, halved, thinly sliced lengthwise
• 2 Tbsp. red wine vinegar
• 1 tsp. sugar
• ¾ tsp. kosher salt, plus more
• 3 Tbsp. extra-virgin olive oil, divided
• 2 large poblano chiles or 3 large Cubanelle peppers or Anaheim chiles (about 8 oz. total), cut in half lengthwise, seeds and ribs removed
• Freshly ground black pepper
• 8 oz. pepper Jack, cut into ½" cubes
• 2 garlic cloves

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