Special equipment: An ice cream maker and a candy or instant-read thermometer
For the ice cream: Whisk the cream, milk, sugar, vanilla and 1/2 teaspoon salt in a medium saucepan and bring to a simmer over medium heat. Beat the egg yolks in a medium bowl. Slowly whisk 1 cup of the hot cream mixture into the beaten yolks, then pour back into the saucepan, whisking, and return to medium heat. Cook, stirring constantly with a wooden spoon, until the mixture thickens, coats the spoon and reaches 180 degrees F on a thermometer, 6 to 8 minutes.
Strain the custard through a fine-mesh sieve into a large bowl or measuring cup; discard the solids. Stir often until the mixture cools to room temperature. Lightly press plastic wrap directly against the surface of the custard to prevent a skin from forming. Chill until cold, about 3 hours. (For faster chilling, set the bowl of custard in a bowl of ice water and stir until cold.)
For the pineapple swirl: Combine the cream, butter and 1/2 teaspoon salt in a measuring cup and set aside. Cook the sugar, corn syrup and 1 tablespoon water in a saucepan over medium heat until the sugar is dissolved, stirring occasionally. Increase the heat to medium high and bring the mixture to a boil. Cook, swirling the saucepan once or twice so that the caramel cooks evenly, until it reaches a medium amber color, about 3 minutes. Remove the pan from the heat and carefully pour the cream mixture into the sugar mixture. Whisk until smooth. Pour about 3/4 cup of the caramel into a measuring cup and set aside.
Stir the crushed pineapple and any juices into the remaining 1/2 cup caramel in the saucepan and return to medium heat. Cook until reduced and thickened, about 12 minutes. Let cool 10 minutes and then process in a food processor until pureed. Chill until ready to use.
Freeze the cold custard in an ice cream maker according to the manufacturer's directions. Transfer half of the ice cream to an 8-inch square metal pan and swirl in 1/2 cup of the pineapple mixture with a butter knife, using circular motions to distribute the pineapple throughout the cream. Add the remaining ice cream and repeat with the remaining pineapple. Cover with plastic wrap and freeze until firm, 2 to 3 hours.
To assemble: Warm the caramel sauce in the microwave at high power for 30 seconds. Put a slice of pound cake in the bottoms of 8 bowls and top with a slice of pineapple, a scoop of ice cream and a dollop of whipped cream. Drizzle with caramel sauce and top with a maraschino cherry.
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