Jason, thank you for taking the time to report this bug and helping to
make Ubuntu better.

This is strange, from your logfile:

Setting up checkbox (0.11.3) ...
Traceback (most recent call last):
  File "/usr/share/checkbox/install/config", line 16, in <module>
    from debconf import Debconf, DebconfCommunicator
ImportError: No module named debconf
dpkg: error processing checkbox (--configure):
 subprocess installed post-installation script returned error exit status 1
No apport report written because MaxReports is reached already
                                                              dpkg: dependency 
problems prevent configuration of checkbox-gtk:
 checkbox-gtk depends on checkbox (= 0.11.3); however:
  Package checkbox is not configured yet.
dpkg: error processing checkbox-gtk (--configure):
 dependency problems - leaving unconfigured

checkbox-gtk can't be upgraded because checkbox (base package) failed to
upgrade. This in turn was caused by absence of (or impossibility to
load) the debconf python module.

What's strange is that debconf, the package which includes the debconf
module for Python, is pretty much impossible to remove without hosing
the entire system, so I'm not sure why it was unable to load during the
checkbox upgrade process.

Jason, just to confirm, I'd like to ask you to perform two tests:

1-

Please let me know whether this file exists on your Maverick system:

/usr/lib/python2.6/dist-packages/debconf.py

2-

a- Open a terminal, type "python" and press enter.
b- At the >>> prompt, type "import debconf" and press enter.
c- Let me know whether you immediately get another >>> prompt (indicating the 
module was loaded) or some error message pops up (in which case, please post it 
here).

Thanks!

** Changed in: checkbox (Ubuntu)
       Status: New => Incomplete

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https://bugs.launchpad.net/bugs/772820

Title:
  package checkbox 0.11.3 failed to install/upgrade: ErrorMessage:
  subprocess installed post-installation script returned error exit
  status 1

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