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I like starting with current known reality and seeing where it might all go.
For a lot of us, it's hard to reconcile a rookie's (or, say, third-year player's) breakout season in real-life with his counterpart's .220/.260/.300 in-game (Adrian Beltre, anybody?)
Keeping rosters up-to-date midseason is fun, for me, to keep myself tuned in to the REAL baseball season. When the off-season starts is when I usually really start playing - I have several months of simming, where I can start a league based in reality and have plenty of time to play through several seasons without real-life contradicting my in-game results. By the time real-life's 2005 season starts contradicting my game world's 2005 season, I'm simming 2012, and contradictions of 2005 performances no longer bother me.
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