Ex) Wipe - 20 Feb 2020

Help - To view further information type /help

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As it stands right now, it just scrolls through the messages, so it may not always line up.

I'd love if the first line, ties to the first line of autoresponse, 2nd to 2nd of auto response so on :)

I think you are configuring the autoresponses wrong.

Every autoresponse should have their own full entry.
Any entry can have multiple triggers to 1 answer or 1 trigger to multiple answers.
This is an example of your first 2 examples.

  "Auto Responses": [
    {
      "Permission": "",
      "Auto Responses": [
        {
          "Is Enabled": true,
          "Remove Message From Sender": false,
          "Send Response For Everyone (true) or Only For Sender (false)": true,
          "Triggers": [
            {
              "Percentage Of Contained Words": 1.0,
              "Regex Enabled": false,
              "Words": [
                "wipe",
              ]
            }
          ],
          "Answers": [
            "Next wipe is 20 Feb 2020'.",
          ]
        },
        {
          "Is Enabled": true,
          "Remove Message From Sender": false,
          "Send Response For Everyone (true) or Only For Sender (false)": true,
          "Triggers": [
            {
              "Percentage Of Contained Words": 1.0,
              "Regex Enabled": false,
              "Words": [
                "help"
              ]
            }
          ],
          "Answers": [
            "To view further information type /help."
          ]
        }