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I paused the Dropbox sync and ran the `rm -R .tox; tox` routine many times without incident, which strongly implicates Dropbox. I'm going to now re-enable Dropbox sync and see if I can trigger the behavior.
Now even with Dropbox updated back to the latest version (16.3.27) and performing the same operations I was two days ago, I've been unable to elicit the behavior. I've confirmed I still have access to delete those files that were being deleted, but yet I can't trigger the failure. Perhaps whatever environmental thing that happened on Monday was a fluke and I'll go back not to being bothered ever by this condition.