I just noticed something: I see you have checkbox 0.16.7, but the latest
is 0.16.8. The man page was renamed in that version, precisely to avoid
this kind of conflict with checkbox-ng.

Could you please try to update your version of checkbox first? Once you
confirm that you have 0.16.8, please retry the upgrade, and it should
work this time.

Still, the proper solution is fixing the packaging, as described in the
previous comment.

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https://bugs.launchpad.net/bugs/1284291

Title:
  package checkbox-ng 0.1-1ubuntu1 failed to install/upgrade: trying to
  overwrite '/usr/share/man/man1/checkbox.1.gz', which is also in
  package checkbox 0.16.7

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