If you are applying the BuildingFootprintDropShadow.cal script make sure you run it on BuildingDropShadow_1K since it does not have a definition query on this layer and all of your buildings will have the cartographic representation applied. Also make sure that the representation rule number is equal to the number you are doing the calculated fields on. For example the rule number is 1, so the rule ID is 1.
If this does not work then you can load the representation rule from the style file. This style file can be from either CM_1.style or any of the other files that get downloaded from the Community Map template. Once you have loaded the representation rule determine which rule number the rule is loaded to, then go to your attribute table for BuildingDropShadow_1K. Do a calculated fields on the RuleID field type number of the representation rule. For example the rule number is mostlikely 2, so type in the number two and click OK. Your representations should appear correct.
Let me know if either of these resolutions help.