The only suggestion I can offer you regarding this workflow is to add a Data Forwarder and place all the remaining steps in a different workflow. You cannot include both Delay and Iterator in the same workflow, as it will cause issues.
This is a general guidance that you can apply for other workflows as well. As for this particular use case, it doesn't appear to be possible for now.
As mentioned previously, I don't think the use case you are trying to achieve is possible, so I won't be able to assist you in setting up the Router conditions.
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Regarding the issue related to file upload, the file does appear to be getting uploaded to the same folder when I tried to upload it manually.
Task History ID: IjU3NmMwNTZlMDYzMTA0MzQ1MjZlNTUzMzUxMzA1MTYwNTQzOCI_3D_pc
However, I'll need to discuss with the team why you are encountering the ScriptError in automation. I'll get back to you with an update soon.