You can only transfer ownership of Google files and folders
Due to this quote, as shown in to How can I transfer ownership of a file in Google Drive that isn't part of Docs? in the past there was no option to attempt transfering ownership of non Google files (PDF, etc.).
However, these days there is. But if you try to use it, it just fails with a "You can't change the owner of this item" message:
What is the logic behind this? Is there any way to bypass this error and transfer such an ownership?