Hmm, after further investigation, I do believe it is a proxy-related
problem (see Bug #24250), not directly connected to apt-cacher.

In fact, if I use a syntax like the following for all the entries in
/etc/apt/sources.list:

  deb http://hostname:3142/it.archive.ubuntu.com/ubuntu/ feisty main

where 'hostname' is the name of the apt-cacher server, the upgrade to
gutsy starts and the channels are correctly updated to gutsy, like in
the following:

  deb http://hostname:3142/it.archive.ubuntu.com/ubuntu/ gutsy main

This does not fix the issue but, at least, it is a workaround to perform
the upgrade using apt-cacher.

-- 
When apt-cacher is used, Update-Manger fails (not #78673 duplicate)
https://bugs.launchpad.net/bugs/113658
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