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It would be great if there was an option in the configuration of the Output Tool to create the output directory if it doesn't already exist. Maybe also to append instead of overwrite for all file types too?
While I certainly appreciate all of the solutions presented here for a batch file workaround (I use the same myself), this feature should be baked into the product.
Or at the very least give the user a checkbox option in the Output tool to create the folder if it does not already exist.