I've found a workaround that works for me.

$ rm -rf $HOME/.update-manager-core
$ update-manager -d # "upgrade" button should appear

What's more, I can reliably reproduce this bug by doing this:
$ rm -rf $HOME/.update-manager-core
$ update-manager
$ update-manager -d # and now it won't be possible to get the "upgrade" button 
to appear

-- 
"update-manager -d" in Feisty presents no option to upgrade to Gutsy
https://bugs.launchpad.net/bugs/129392
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