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Like Shucker I play every season, every game (that my team is involved in, though not always every pre-season exhibition game), every inning, every at-bat, in 1 pitch mode. And I play out All-Star games and all post-season games (even when my team isn't involved), though in my league that only involves a World Series, no playoffs.
Unlike Shucker I do not play games to correspond to the calendar in-season (IRL) but move ahead at my own pace. And I probably spend way more time playing OOTP then might be healthy (but single and childless and with few obligations, so it works for me.)
It looks like I am probably averaging about 5-7 seasons per OOTP version.
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