Need automation notification help

I am new to Smartsheet and need help automating notifications if specific conditions are met. I called our IT department, and the expert could not help. She said that each condition follows an "and" logic, not an "or," so she was asking me to create an individual automation workflow per condition. Is this true? This seems to counter how smartsheet designed its automation. There may be something that I set up regarding the conditions that are stopping the automation. Note: not sure why the last two conditions are both numbered as 3. The trigger for now is when a date is reached daily. Attaching the screenshots (the last column is the assigned to, and it is a contact list column)

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