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I haven't played enough to say for sure but I recently just started a fictional MLB setup and made the WS in my first year with my team. I didn't make any trades and made only a few waiver moves. I guess you could say it was luck of the draw with my team.
In the old version of OOTP, after I got used to the game, I found it extremely easy to build perpetual playoff teams. Some people implement "house rules" to not take advantage of the AI. I don't like to do that. I think you get your best challenge from playing OOTP in an online league. I'd recommend you check one out in addition to your solo play.
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