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I guess it didn't attach last time, my apologies. I had considered the cross tab tool, but wasn't sure how to make it work when I only have one column? I will take another look, maybe I missed something.
I attached a workflow that should be able to get you the output you're looking for (I put most of your data from your picture into the Text Input). The key was to use a couple Multi-Row Formula tools in order to get the groupings right for the Cross Tab. I went ahead and also added a normal Formula tool, too, to create custom headers for your new fields. You could have also left this out and used New Field as your headers and changed them later on with a Select tool or something.