If it helps, in software-center, we set the menuitems to be
sensitive/insensitive when the toplevel menuitem is activated.

So in:
on_menuitem_edit_activate()
we check a few things and then:
menuitem_copy.set_sensitive()
based on these checks.

Is it maybe that appmenu isn't sending out these activate signals? Or
that it is dynamically updating the sensitivity of the items? If you
need some more info on how SC's menus are working, please don't hesitate
to post a reply.

-- 
Menu items not insensitive/disabled after application start
https://bugs.launchpad.net/bugs/603479
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