Beat butter at medium speed with a heavy-duty electric stand mixer until creamy; gradually add sugars, beating well. Add molasses and orange extract, beating well. Combine flour and next 3 ingredients. Add to butter mixture alternately with beaten eggs, beginning and ending with flour mixture. Beat well after each addition.
Combine candied pineapple, chopped cherries, and next 4 ingredients in a large bowl; sprinkle with 1/2 cup flour, stirring to coat well. Stir fruit into batter. Spoon batter into 3 heavily greased and floured 8 1/2" x 4 1/2" loaf pans. Arrange additional cherries and pecans on top of batter, if desired.
Bake at 250° for 2 1/2 hours or until a wooden pick inserted in center of loaves comes out clean. Brush each loaf with 1 Tbsp. brandy, if desired. Let cool completely on a wire rack. If desired, wrap loaves in brandy-soaked cheesecloth. Store in an airtight container in a cool place up to 3 weeks. Pour a small amount of brandy evenly over loaves each week, if desired.