Hi @LloydBirch thanks for sharing the information. I would recommend building the workflow directly in the workflows tool as you will see more functionalities there. As you can see at the bottom you can click on ‘Open in Workflows’. That way you can set re-enrollment triggers if needed.
One important aspect regarding lifecycle stages is that they can’t go back unless you clear the property first (using ‘clear property value’ in a workflow, or manually. So if you want to take a contact back to lead, you first need to clear the lifecycle stage and then you can assign the new value - ‘lead’. You can create a list of contacts that you want to clear their lifecycle stage and use it as an enrollment trigger.
The issue you’re seeing with the contact is probably because you have auto-sync on between company’s lifecycle stage and contact. This means that if the company has the lifecycle stage in opportunity, any contact associated with that company will be assigned the same lifecycle stage.
I recommend revising these two resources to clarify.
Hope this helps!