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tests: Improve coverage on `directory_ls` endpoints

Antoine R. Dumont requested to merge generated-differential-D3694-source into generated-differential-D3694-target

Prior to this commit, when listing a directory, we did not check up to the contents. This fixes it.

This also fixes one inconsistent test data and the tests impacted by this change.

Detected in !989 (closed)

Test Plan

tox

Migrated from D3694 (view on Phabricator)

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