First, I disagree with the premise of the first statement, but it doesn't matter, because this whole line of argument is an irrelevant red-herring. The reason is because as everyone well knows, what tipped the election for Baby Bush was not his "preparedness", it was his charisma vis-a-vis Gore. This was well covered and reported during the election. People like Bush more because he was "the kind of guy you felt like you could have a beer with", whereas Gore was stiff and un-personable (like Hillary). So you're trying to make the argument about who was "more/better prepared" Gore or Bush, but that is not the issue, because the election, as we all know did not turn on that.Bush was better prepared in 2000. Rove's GotV machine swung the election.
Second, these two statements are two unconnected things that are not remotely dependent on the other anyway. Rove's "machine" as you call it was involved in much more meta-issues than Dubya's so-called "preparedness". Third, the connection you are trying to imply is a non-sequitur. If you are attributing the victory to the "Rove political machine" then it wasn't due to Dubya's staying up all night cramming. If you're attributing the win to Bush's ability to personally out-prepare Gore... well then where does Rove's machine come in?