In large glass or plastic bowl, stir pineapple, 1 cup sugar and the rum until mixed. Cover and refrigerate at least 4 hours.
In medium bowl, mix 2 cups flour and the salt. Cut in shortening, using pastry blender (or pulling 2 table knives through ingredients in opposite directions), until particles are size of small peas. Sprinkle with cold water, 1 tablespoon at a time, tossing with fork until all flour is moistened and pastry almost cleans side of bowl (1 to 2 teaspoons more water can be added if necessary).
Gather pastry into a ball. Divide in half; shape into 2 flattened rounds on lightly floured surface. Wrap in plastic wrap; refrigerate about 45 minutes or until dough is firm and cold, yet pliable. This allows the shortening to become slightly firm, which helps make the baked pastry more flaky. If refrigerated longer, let pastry soften slightly before rolling.
Heat oven to 425ºF. With floured rolling pin, roll 1 pastry round into round 2 inches larger than upside-down 9-inch glass pie plate. Fold pastry into fourths; place in pie plate. Unfold and ease into plate, pressing firmly against bottom and side.
Drain pineapple, reserving juice. Spoon pineapple into pastry-lined pie plate. In 1-quart saucepan, mix 1/2 cup sugar, 1/2 cup flour, the cinnamon and nutmeg. Stir in 1/2 cup of the reserved juice (reserve remaining juice). Heat to boiling, stirring constantly. Boil and stir 1 minute; remove from heat. Stir in butter. Pour over pineapple. Trim overhanging edge of pastry 1 inch from rim of pie plate.
Roll other round of pastry into 10-inch round. Cut round into 1/2-inch strips. Place 6 strips across filling. To make lattice top, weave a cross-strip through center by first folding back every other strip going the other way. Continue weaving lattice, folding back alternate strips before adding each cross-strip, until lattice is complete. Trim ends of strips. Fold trimmed edge of bottom crust over ends of strips, building up a high edge; seal and flute. Cover edge with 3-inch strip of foil to prevent excessive browning during baking.
Bake 35 to 45 minutes or until crust is brown and filling is bubbly, removing foil for last 15 minutes of baking.
In medium bowl, beat cream cheese with electric mixer on medium speed, gradually adding 1/4 cup plus 2 tablespoons reserved pineapple juice until smooth and creamy. Serve with pie.