When I export a file of the same name (ex. "Adobe Video - V1"), I get the two confirmations that I'm replacing the file of the same name. I click "Okay" on both prompts, but when I press export, I get the attached error message. I never had this problem before, any ideas as to what it could be?
Sort of a catch 22. If you don't import the file into your project, you can replace it using the export. If you import it into the project (either directly or via the export settings option, under "General" for "Import into project"), export won't let you replace it.
And renaming the file inside PR still does not allow the export. Even though the PR project name is changed, the file on disk is the same and PR won't allow it.
I think you'd have to delete the file first. Renaming on disk does not work, because it leaves the original name as the PR name in the project. As soon as you rename on disk, PR displays the link media dialogue for you to relink - to the new name or offline. There may be a way, but I did not find it. I'd just use a new name.