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See if the attached workflow gets you started going in the right direction. This gets the summed records you're looking for. Then you can use the Union tool to add these records back to your dataset. If you still need assistance, please provide specific details on where you're still having issues.
I'm glad you're able to make some progress. If you want to change the date fields, you can either add a Formula tool after each of the Summarize tools or you can use Dynamic Rename tools after the Cross Tab tools.