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I'm a little confused. Why hasn't anybody mentioned Stratomatic Baseball? I played six seasons of it (1996-2001), and it was in many ways better than OOTP, especially as regards actual play of the games. Admittedly it's nowhere as far as scouting, player development, financials, minor leagues, etc., but it does provide you with better lefty/righty matchups, ability to limit the playing time of players who didn't play much in a season (those supersubs).
The support for the deadball era is spotty. Only 1911 and 1920 got the 'deluxe' treatment, five other seasons got 'special' treatment and the other thirteen use some degree of estimated stats. From 1959 to the present, statistical recreation is vastly superior in Stratomatic to what I've found in OOTP, and that's based on the state of the game four years ago; it improved every year that I played it.
If all you're interested in is trading and game day managing, I'd strongly suggest checking out Stratomatic. The only reason I no longer play is that it's not Mac compatible.
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