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Fair points
I agree in this case, where both teams were under .500, its a little more difficult to find sympathy for the owner who lost when it is debatable if he played his best team all year.
But regardless of the specifics in this instance, I still think in general having a managed team get some preference once in a while is warranted - and it seems to me the chance to participate in the playoffs is a good time for the managed team to get the advantage. Maybe getting to be in the playoffs gets the owner back into more? I just don't see the downside to having someone who has particpated in a league, possibly for years, finally getting their playoff shot over the robot manager.
I suppose the idea of forcing the managed owner to try just a bit harder to win is a valid one, as it might stir up some trades and such.
But ultimately I'd rather the guy who has paid his $100+ for the year get a chance to play a few more games.