Crispy Garlic Potato Skins with Spicy Roasted Tomato Ketchup

Name: Crispy Garlic Potato Skins with Spicy Roasted Tomato Ketchup
Ingredients: 2 1/2 pounds ripe tomatoes; 2 tablespoons extra-virgin olive oil; 1 medium onion, finely diced; 2 cloves garlic, minced; 2 canned chipotle chiles en adobo with the sauce that clings to them, chopped; 1/4 teaspoon ground cinnamon; 1/4 teaspoon ground allspice; Pinch ground clove; 1/4 cup cider vinegar; 1 tablespoon dark brown sugar; 1 teaspoon kosher salt, plus more as needed; Freshly ground black pepper; 4 medium russet potatoes (about 2 pounds), scrubbed; 4 cloves garlic, smashed; 1/4 cup extra-virgin olive oil; Kosher salt