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I'd suggest doing a season replay at first. Everything is already set up for you -- rosters, lineups, rotations, etc. All you have to do is take over a team and go from there. If you like historic seasons, choose one with an interesting pennant race, like 1908, 1951, 1964, or 1978. Then you can move on to making your own leagues. OOTP is as easy or as in-depth as you want to make it. After a short time, 95% of everything you do will be intuitive.
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