Preheat oven to 350°F. Line a rimmed baking sheet with aluminum foil; set a wire rack inside the baking sheet. Stir together bourbon, 1 cup of the preserves, and 1/3 cup of the brown sugar in a small bowl. Place ham on a large piece of aluminum foil big enough to cover entire ham; brush with 1/2 cup of the bourbon glaze. Wrap tightly in aluminum foil. Place, cut side down, on prepared wire rack. Add 3 cups water to baking sheet under rack. Bake ham 2 hours.

Meanwhile, heat a large cast-iron skillet over high until very hot. Add pineapple; cook, stirring occasionally, until browned on 2 to 3 sides, about 10 minutes. Reduce heat to medium; add coconut oil, chile, and ginger. Cook, stirring often, until softened and fragrant, about 2 minutes. Add salt, allspice, and remaining 1/4 cup preserves and 2 tablespoons brown sugar. Cook, stirring often, until liquid has mostly evaporated, about 4 minutes. Remove from heat; stir in lime juice. Transfer mixture to a bowl; cool to room temperature, about 20 minutes.

Remove ham from oven; remove foil. Increase oven temperature to 425°F. Baste ham with 1/2 cup of the bourbon glaze, brushing in between slices. Return to oven; bake, uncovered, at 425°F for 15 minutes. Remove from oven; brush with remaining 1/2 cup glaze. Continue baking, uncovered, until a thermometer inserted in thickest portion of ham registers 140°F, about 15 minutes. Remove from oven; rest 10 minutes. Slice and serve with pineapple chutney.