Advice + WorkFlow Automations + Errors Duplicating Tasks

I need help understanding why my WorkFlow Automations are duplicating scheduled activities/tasks etc. I am sure it is user error, however it is currently invalidating  our tracking numbers by doubling or tripling the planned to-dos and completed numbers. There are also occasions where the automations will not become triggered and is now making our process less than efficient. 

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The error I am referencing.
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What the planned tasks should automatically look like via Workflow Automation
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