Two People Assigned - Completing at Different Times

I am looking for feedback about ways to automate assigning two people to the same task - but they have separate roles to complete said task.
Let me explain our use:

We are building a “Life Events form” for when an employee has a life event that our Marketing and HR team need to acknowledge (new baby born, marriage, employee moved, etc). Usually, this requires one individual on our team to update some of our databases and maybe send a card. So, I know I can build an automation that when a new item comes in, assign that person. However, on occasion the life event requires a gift to be sent. Here, we need the initial person to be assigned for her database updates and we need a second person from our team assigned to pack and mail the gift.

Where I am struggling is that if I build an automation that assigns them both the item if “mail gift” is chosen - then when one of them finishes their portion, the item will be marked as done and get off of the radar or “My Work” of the other person.

Are there any good ways to set this type of thing up that will be an automation following a form item added - so they both can get assigned individual tasks? I played around with doing “if this is selected, duplicate item” and then having the second person assigned to that next item. But it resulted in a looping duplication series because it kept feeding off of itself.

I also considered an automation that would create a subtask for the second person. But, there seemed to be no way to then have the date be auto assigned for that subtask which is crucial to our workflow.

Any feedback would be great!