A note: I suppose this type can slide this time, but we should keep the topics mainly pertaining to a specific event or series of events, rather than an issue or idea.
It sounds like you are talking about a large scale election, specifically a presidential one. Voter strategy applies here a lot. If a voter chooses candidate A over candidate B, it is because they believe A is better. Now if they actually support a candidate C, but vote A only because B is worse, then assume C is unpopular and has little chance of winning. If someone's ballot is a write-in for Mickey Mouse, well heck, that's voting against everyone else too, but accomplishes nothing. This is why candidates attempt to centralise the vote as much as possible by appealing to the greatest amount of people. During primaries, candidates who drop out often put their support behind another guy, so that votes are not wasted. With your example, there's no misrepresentation; it's more about who are the smarter voters. Incumbency is only an advantage if the track record was good, and is otherwise unrelated. (Also, if the percentages are that close, a recount is likely.)
I agree that current voting systems might seem a little unfair... but I also agree with PopperMan, that there isn`t really a 'fair' solution, considering it is more about the electoral votes, rather than population.
Which system is more fair is quite debatable. In a society that was far different than today's, the intent of the electoral college was to level the playing field and diminish regional voting power. One might also argue that electing to the nation's highest office deserved a contrast to direct vote for Congress and the president's handpicking for the Court. There was much care to avoid the pure democracies of old.
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