Create a permalink to a pdf?

You can accomplish the first part using the Quick Page/Post Redirect Plugin. Just set the Request URL to /resume and the Destination URL to /wp-content/uploads/2021/07/Resume-v4.pdf

For the second part of your question, you can add a redirect rule to your .htaccess file:

Redirect /wp-content/uploads/2021/07/Resume-old.pdf /resume

The way you worded your question you actually would set up an infinite redirect, so I changed it here to “Resume-old.pdf”.

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