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If the devs wanted to they could program the AI to make it so elite a human player would barely stand a chance.
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This ^ is what I'm looking for in a good baseball stragety sim. But, in a way that makes it somewhat fair to the player (human) me and I still have a "chance" if I do everything right.

I mean as it is now even on hard or hardest trading settings I can still finagle the trade I want if I take enough time to do it. A lot of it falls to being able to pick up cheap good guys still in the FA pool. They should have the AI try to DRAIN the AI pool every year as much as possible.
I do have to disagree with you about no game is perfect. Front Page Sports Baseball came about as close to perfect as they came. I do remember the trading of players was a lot harder than it ever has been with Out of the Park. I honestly believe their trading system was setup on a player for player point system and the numbers had to match pretty darn close to be able to get a trade. This game if you throw enough money and other crappy players at the computer AI it will accept not taking into account everything it should have. I think a lot of it has to do with basically unlimited players to get in the FA pool and in Front Page Sports Baseball you couldn't do that. There were limits.