I wrote a tiny python test case for this (it requires a installed
monodevelop and a otherwise clean autoremove info):

    def test_remove_bug659111(self):
       cache = apt.Cache()
        cache["monodevelop"].mark_delete()
        for pkg in cache:
            if pkg.marked_install:
                print "inst: ", pkg.name
            if pkg.marked_delete:
                print "rm: ", pkg.name
            if pkg.is_auto_removable:
                print "auto-removable: ", pkg.name

This prints for me:
inst:  libwebkit1.1-cil
inst:  monodoc-browser
rm:  monodevelop
auto-removable:  monodevelop
auto-removable:  monodoc-base
auto-removable:  monodoc-manual

But at the point that monodoc-browser is marked for install monodoc-base
is no longer autoremovable.

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https://bugs.launchpad.net/bugs/659111

Title:
  Installing then removing Monodevelop reports "the package system is
  broken"

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