So after another chat session regarding an item I sold 6 days ago but still no funds released, I have been told;
Agree to purchase the pre-paid label.
Download it.
Go back to the order where you can now see tracking info.
Change the tracking number to whatever number you used yourself.
This is the answer to my situation, albeit that it takes a bit more effort on my part. The eBay representative assures me that they are constantly working on improving sellers experience.
I'm sure that given time, all this will get better/easier, just not convinced that less tech-savvy newcomer's to eBay will see it being worth the hassle.